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Vacation Rentals in Monterey, MA and nearby

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    From
    $1,656
    / Week
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7
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    From
    $364
    / Night
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    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveller has booked this property
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    $232
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    1 / 13
    4.5 of 5 stars (14) Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other traveller has booked this property
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    Overview Reviews (14)

    The following rentals are within 15 kilometres of Monterey, Massachusetts.

    From
    $172
    / Night
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Horse Riding Nearby
    • Washer
    • Central Heating
    • Dryer
    • Cooker
    • Housekeeping...
    • Wi-Fi
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    From
    $396
    / Night
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • There Are Tennis...
    • Air Conditioning
    • Watersports Nearby
    • Deck
    • TV
    • Washer
    • DVD Player
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $2,119
    / Week
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    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Grill
    • Dryer
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Refrigerator
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
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    Location Information
    New Marlborough, Berkshires 01230
    From
    $497
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Watersports Nearby
    • Housekeeping...
    • Hot Tub
    • TV
    • There Are Tennis...
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 24 July 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed 22 July 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
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    From
    $331
    / Night
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    Great Barrington
    5 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Deck
    • Stereo System
    • Wi-Fi
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to my dream come true! Pick from your own orchards, vegetable gardens and perennial beds. Swim in your own Green River or your beautiful heated swimming pool. And of course, SKI, SKI, SKI!! This home is beautiful four seasons of the year. Major highlights include a fireplace in the kitchen... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $3,245
    / Week
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    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • Deck
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $331
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Mountain Views
    • DVD Player
    • Stereo System
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
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    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed 20 May 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    From
    $343
    / Night
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    Tyringham
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Dryer
    • Washer
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $5,960
    / Week
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    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Playground
    • Internet Access
    • Mountain Views
    • Fireplace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $464
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    other travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Satellite TV
    • Stereo System
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 5 February 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
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    $464
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    1 / 22
    5 of 5 stars (11) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (11) Make Enquiry
    Overview Reviews (11)
    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Fireplace
    • TV
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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    Location Information
    Lee, Berkshires 01260
    5 of 5 stars Reviewed 3 September 2015
    Mary has created the most beautiful family vacation home. The pictures are beautiful but don't do the home justice. It is lovely and immaculate. The home is stocked with...
    5 of 5 stars Reviewed 28 August 2015
    We loved the online description of the South Lee schoolhouse and were not disappointed. The house exceeded our expectations. The locations is superb, minutes from almost...
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    From
    $695
    / Night
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    1 / 35
    5 of 5 stars (16) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (16) Make Enquiry
    Overview Reviews (16)
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • DVD Player
    • Stereo System
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    From
    $470
    / Night
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 11
    other travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Overview Reviews (8)
    Amenities & Details
    • Mountain Views
    • Central Heating
    • Water Views
    • DVD Player
    • TV
    • Stereo System
    • Deck
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
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    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed 27 September 2014
    We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
    5 of 5 stars Reviewed 3 September 2014
    This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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    $662
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    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield
    4 Bedrooms, 3 Bathrooms, Sleeps 15
    Overview Reviews (8) Make Enquiry
    Overview Reviews (8)
    Amenities & Details
    • Deck
    • Hot Tub
    • Shared Outdoor Pool...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting,... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed 6 August 2014
    Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
    5 of 5 stars Reviewed 23 February 2014
    Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
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    From
    $232
    / Night
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    South Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    Location Information
    South Lee, Berkshires 01260
    From
    $265
    / Night
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6
    other traveller has booked this property
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    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $596
    / Night
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    1 / 17
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Central Heating
    • Fireplace
    • Internet Access
    • Washer
    • Mountain Views
    • Hot Tub
    • Dryer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed 12 June 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    $1,656
    / Week
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    1 / 15
    5 of 5 stars (1) Excellent
    Sandisfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Horse Riding Nearby
    • Wi-Fi
    • DVD Player
    • Shared Tennis Court
    • Central Heating
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
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    Location Information
    Sandisfield, Berkshires 01255
    5 of 5 stars Reviewed 1 September 2015
    We had a great experience at this house. This house exceeded our expectations. It is bright and open with a big screened porch overlooking the woods and a beautiful garden. It...
    5 of 5 stars Reviewed 1 February 2015
    We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch...
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    $894
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $397
    / Night
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Fireplace
    • DVD Player
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Internet Access
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $298
    / Night
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Stereo System
    • Central Heating
    • Internet Access
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed 14 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
    3 of 5 stars Reviewed 4 July 2015
    On the water with canoes, close to Tanglewood, but tired amenities. Poor second bedroom, not yet cleaned until after we arrived, but most unfortunate it was a very hot weekend...
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    $331
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Dryer
    • Satellite TV
    • Washer
    • DVD Player
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock... View all property information
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    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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    From
    $993
    / Night
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $662
    / Night
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    Tyringham
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Central Heating
    • Satellite TV
    • Staffed Property
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Mountain Views
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $662
    / Night
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly... View all property information
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    Stockbridge, Berkshires 01262
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    $464
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Deck
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
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    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed 4 January 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Garage
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 17 June 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    1 / 10
    5 of 5 stars (15) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3
    other travellers have booked this property
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    Amenities & Details
    • Boat Available
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
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    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed 27 August 2015
    I stayed in the cottage with my girlfriend and our small dog and we had a fantastic time! The cottage had everything we needed (wifi, large bathroom, dining table, cable TV) and...
    5 of 5 stars Reviewed 25 August 2015
    My husband, 5 year old daughter and I had a great time at the Sigel's. The views are spectacular and we enjoyed being at the pool, going hiking and visiting the Rockwell museum in...
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    $305
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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Make Enquiry
    Overview
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    • Refrigerator
    • Linens Provided
    • Cooker
    • Fireplace
    • Mountain Views
    • Wi-Fi
    • Deck
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying... View all property information
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    Great Barrington, Berkshires 01230
    From
    $1,589
    / Week
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    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Patio
    • Dryer
    • TV
    • Washer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming get-a-way in a friendly residential neighborhood in Great Barrington. Our home is sunny and bright, with an eat-in-kitchen, casual living room and dining area with beautiful picture windows, three comfortable bedrooms, and 1.5 bathrooms. Fully furnished with an eclectic mix of modern and... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $298
    / Night
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Fireplace
    • TV
    • Stereo System
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
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    $232
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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 16 August 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    $662
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    Great Barrington
    3 Bedrooms, 8 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Ping Pong Table
    • Game Room
    • Satellite TV
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    SummerStone is an elegant country home beside a state forest the NYT once referred to as 'the best kept secret in the Berkshires'. Enjoy red oak floors, tumbled marble showers, cozy fireplaces and soaring ceilings. Go kayaking, biking, swimming or hiking then relax on the 600 sq. ft. porch. Ping... View all property information
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    Location Information
    Great Barrington, Berkshires 01258
    From
    $331
    / Night
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
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    Tyringham, Berkshires 01264
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    $199
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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
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    Amenities & Details
    • TV
    • Refrigerator
    • Wi-Fi
    • Waterfront
    • Cooker
    • Linens Provided
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 13 July 2015
    I just got back from my weekend stay here last night, and if I hadn't been so tired, I would have posted this review already! I was absolutely thrilled with this rental - where...
    4 of 5 stars Reviewed 21 June 2015
    Lovely home, great location, walking distance to the town of Stockbridge. Many things to see and do while we stayed for our five day trip. Must see: Naumkeg, Shrine of Divine...
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    $661
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    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12
    other travellers have booked this property
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    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Sauna
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 3 December 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed 18 July 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    $205
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 5
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Horse Riding Nearby
    • Patio
    • Grill
    • Watersports Nearby
    • Cooker
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is the second floor of the barn. Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot pot and coffeemaker. Bathroom has... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $331
    / Night
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    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Washer
    • Mountain Views
    • Deck
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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    Great Barrington, Berkshires 01230
    From
    $298
    / Night
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Overview Reviews (5)
    Amenities & Details
    • Boat Available
    • There Are Tennis...
    • Watersports Nearby
    • Fireplace
    • Satellite TV
    • Washer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    4 of 5 stars Reviewed 24 October 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Water Views
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Location Information
    Stockbridge, Berkshires 01260
    From
    $265
    / Night
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Linens Provided
    • Cooker
    • Refrigerator
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
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    Great Barrington, Berkshires 01237
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    $199
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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed 17 June 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    $497
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Shared Indoor Pool
    • Shared Tennis Court
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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    Lee, Berkshires 01238
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    $2,252
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    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Porch
    • Deck
    • DVD Player
    • Washer
    • TV
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
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    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed 2 February 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    $89
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1
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    Overview
    Amenities & Details
    • Patio
    • Wi-Fi
    • Refrigerator
    • There Are Tennis...
    • Satellite TV
    • Central Heating
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a... View all property information
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    Lee, Berkshires 01238
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    $616
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    1 / 33
    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveller has booked this property
    Overview Reviews (3) Make Enquiry
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    Amenities & Details
    • Game Room
    • Stereo System
    • Boat Available
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $331
    / Night
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    1 / 13
    5 of 5 stars (2) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Stereo System
    • Washer
    • Air Conditioning
    • Satellite TV
    • Fireplace
    • DVD Player
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 26 May 2015
    This home is beautiful! It is an older home, and comes with the charm and quirks, which make it even more lovely! The décor is modern, simple and fits the house wonderfully. The...
    5 of 5 stars Reviewed 22 January 2015
    This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night. The surrounding...
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