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Vacation Rentals in Lenox, MA and nearby

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    All 28 Rentals in the Lenox Area
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    $184
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
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    $492
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    1 / 24
    Lenox
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    $297
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    1 / 15
    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $492
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    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    Amenities & Details
    • TV
    • Central Heating
    • Washer
    • Mountain Views
    • Stereo System
    • Internet Access
    • Dryer
    • Playground
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    Lenox, Berkshires 01240
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    1 / 14
    Lenox
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    Location Information
    Lenox, Berkshires 01240

    The following rentals are within 10 kilometres of Lenox, Massachusetts.

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    1 / 21
    5 of 5 stars (3) Excellent
    Lee
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • TV
    • Fireplace
    • DVD Player
    • Grill
    • Mountain Views
    • Washer
    • Wi-Fi
    • 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 19 April 2015
    This is a very special place to stay in the Berkshires! Not only is its location perfect for getting to Tanglewood, Jacobs Pillow, Stockbridge, and most other Berkshires...
    5 of 5 stars Reviewed 17 April 2015
    Friends and I gathered for two days at this rental. It was everything that we could have desired and more: great location, nearby walks, a roomy and perfectly maintained rental...
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Deck
    • Washer
    • Playground
    • Air Conditioning
    • Internet Access
    • Dryer
    • Refrigerator
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $246
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    1 / 8
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Parking
    • Internet Access
    • Garage
    • Fireplace
    • Linens Provided
    • Hot Tub
    • Mountain Views
    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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    Location Information
    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 / 17
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Washer
    • Refrigerator
    • Internet Access
    • Grill
    • Central Heating
    • Hot Tub
    • Mountain Views
    • Dryer
    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 / 19
    5 of 5 stars (14) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Reviews (14) Make Enquiry
    Amenities & Details
    • Deck
    • Dryer
    • There Are Tennis...
    • Washer
    • Satellite TV
    • Central Heating
    • Horse Riding Nearby
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 20 May 2015
    We came from all over the northeast for a family get together, and were thrilled with the house. Plenty of room, clean and nicely decorated, close to all the Berkshires have to...
    5 of 5 stars Reviewed 20 April 2015
    We spent 3 nights here, 2 with sons, daughters in law and four grandchildren. There were plenty of bedroom plus a foldout couch, and the kitchen was very well equipped. One of...
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Refrigerator
    • Linens Provided
    • Satellite TV
    • Internet Access
    • Dryer
    • Fireplace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    • Stereo System
    • Fireplace
    • Mountain Views
    • Dryer
    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
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    $442
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    1 / 33
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    travellers have booked this property
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Washer
    • Central Heating
    • Porch
    • DVD Player
    • Grill
    • Internet Access
    • Refrigerator
    • Dryer
    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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    1 / 4
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    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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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Mountain Views
    • Private Fishing...
    • Dryer
    • Refrigerator
    • Central Heating
    • Washer
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting.... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
    5 of 5 stars Reviewed 25 August 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    $737
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    1 / 3
    3.5 of 5 stars (3) Average
    Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Internet Access
    • Cooker
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Shared Indoor Pool
    • Gym
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc. View all property information
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    Location Information
    Lee, Berkshires 01238
    3 of 5 stars Reviewed 14 October 2014
    We were in the older condos that need new furnishings, tvs, appliances, etc. I recommend trying to get into the newer condos; but not the older units; thus my rating below...
    4 of 5 stars Reviewed 14 July 2014
    My wife and I spent a restful week at The Oak and Spruce resort in the Berkshires. The unit was roomy and had a large master bedroom with jacuzzi and shower.The second bedroom had...
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    $289
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    1 / 24
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Stereo System
    • Dishwasher
    • Parking
    • DVD Player
    • Fireplace
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Both bathrooms are newly repainted. New carpeting. Wireless Door Locks. Fireplace and central heating. Snow shoes. Cross country skis included. Experience a Berkshire get-away in this huge secluded luxury modern house. It&39;s the only house that is surrounded by 10,000 Acres of protected... View all property information
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    Location Information
    Lee, Berkshires 1070
    From
    $553
    / Night
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    Amenities & Details
    • Washer
    • Fireplace
    • Deck
    • Satellite TV
    • Dryer
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $922
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    1 / 7
    Lee
    5 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    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
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    $215
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    1 / 2
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    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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    Location Information
    Lee, Berkshires 01238
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    1 / 10
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Linens Provided
    • Balcony
    • Terrace
    • Towels Provided
    • Patio
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
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    Location Information
    Lee, Berkshires 01238
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    Lee
    1 Bedroom / 1 Bathroom / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    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
    $461
    / Night
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    Amenities & Details
    • Air Conditioning
    • Sauna
    • Hot Tub
    • Internet Access
    • Gym
    • Shared Indoor Pool
    • DVD Player
    • Washer
    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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    Location Information
    Lee, Berkshires 01238
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    1 / 12
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Porch
    • Internet Access
    • Linens Provided
    • Satellite TV
    • Mountain Views
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
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    Location Information
    Lee, Berkshires 01238
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    $307
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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
    Amenities & Details
    • Cooker
    • Mountain Views
    • Satellite TV
    • Refrigerator
    • DVD Player
    • Internet Access
    • Dryer
    • Stereo System
    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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    2 of 5 stars (1) Poor
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
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    Amenities & Details
    • Satellite TV
    • Linens Provided
    • Terrace
    • Water Views
    • Parking
    • DVD Player
    • Towels Provided
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Berkshires, in Western Massachusetts, are known as center of cultural activities, including but not limited to Tanglewood (the summer home of the Boston Symphony Orchestra), Shakespeare Theatre Festival, Jacobs Pillow, Williamstown Theatre Festival, plus numerous recreational opportunities for... View all property information
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    Richmond, Berkshires 01254
    2 of 5 stars Reviewed 10 September 2014
    I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The...
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    1 / 10
    Richmond
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    In 1832, Josiah Loomis bought a parcel of land 'and the structures thereon', along what was then known as 'Massachusetts Turnpike No. 10,' the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $369
    / Night
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    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Mountain Views
    • Satellite TV
    • Stereo System
    • DVD Player
    • Horse Riding Nearby
    • There Are Tennis...
    • Game Room
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
    Make Enquiry
    Location Information
    West Stockbridge, Berkshires 01266