We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in New Marlborough, MA and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $383 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite New Marlborough area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 10
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection

    The following rentals are within 25 kilometres of New Marlborough, Massachusetts.

    1 / 20
    5 of 5 bubbles (6) Excellent
    West Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 32
    5 of 5 bubbles (4) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 16
    5 of 5 bubbles (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Porch
    • Parking
    • Washer
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles 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 bubbles 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...
    See all reviews
    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master... View all property information
    Location Information
    Stockbridge, Berkshires 01238
    1 / 10
    5 of 5 bubbles (1) Excellent
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 18 October 2016
    We had a wonderful time staying at this property. The house is full of charming details - we kept discovering art objects till the time of our departure. The kids had fun using...
    See all reviews
    1 / 25
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 1 week ago
    Me & my son Josh had a lovely stay at the cottage. Ruth was very pleasant, the place was clean and the location was perfect. We were provided with wood for fire, the kitchen has...
    See all reviews
    1 / 11
    3.5 of 5 bubbles (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 bubbles Reviewed 21 July 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 bubbles 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...
    See all reviews
    1 / 52
    5 of 5 bubbles (9) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores,... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 bubbles Reviewed 3 weeks ago
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
    5 of 5 bubbles Reviewed 19 July 2016
    From the moment we turned off the beautiful country road and into River Song's driveway my wife and I sensed we were in for a treat. Barbara and Phillip came out to meet us and...
    See all reviews
    1 / 8
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles 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...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 20
    5 of 5 bubbles (25) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 9 May 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
    5 of 5 bubbles Reviewed 30 March 2016
    Some girlfriends and I decided to meet up for a weekend and found this wonderful home which was super convenient for all of us - some coming from MA others from upstate NY. When...
    See all reviews
    1 / 4
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles 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...
    See all reviews
    1 / 6
    Lee
    1 Bedroom, 3 Bathrooms, Sleeps 5 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Shared Garden
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 12
    4 of 5 bubbles (1) Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 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
    Location Information
    Lee, Berkshires 01238
    4 of 5 bubbles Reviewed 12 August 2016
    We stayed at Jo-Anne's cottage for a week in mid-July. Wasn't sure what to expect as the place had no reviews. Our hostess made us feel at home right away and made a major...
    See all reviews
    1 / 22
    5 of 5 bubbles (2) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Shared Indoor Pool
    • Satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    220 acres with tennis, indoor & outdoor pools, yoga studio, gym and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 11 August 2016
    The Playhouse is a magical place to connect with friends and family. There are a half dozen living spaces that offer anything from quiet reading areas with a view, to 40 person...
    5 of 5 bubbles Reviewed 11 August 2016
    I didn't want to leave. The view from the picture window is breathtaking. The home has more space than even our large group could fill. If you are a yogi, you can enjoy your own...
    See all reviews
    1 / 30
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 23 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
    See all reviews
    1 / 10
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Mountain Views
    • Outdoor Dining Area
    • Balcony
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 2
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles 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...
    See all reviews
    1 / 11
    5 of 5 bubbles (1) Excellent
    Falls Village, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area.... View all property information
    Location Information
    Falls Village, Connecticut 06031
    5 of 5 bubbles Reviewed 18 September 2016
    I only wish my mobility was better to take a walk on this beautiful property very close to Lime Rock Park and many other cultural attractions. Owners were very nice and obviously...
    See all reviews
    1 / 12
    5 of 5 bubbles (4) Excellent
    Alford
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural... View all property information
    Location Information
    Alford, Massachusetts 01266
    5 of 5 bubbles Reviewed 16 October 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked goods...
    See all reviews
    Get the List
    1 / 17
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 42
    5 of 5 bubbles (3) Excellent
    Lakeville, CT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Porch
    • Washer
    • Satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This newly renovated 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. This house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove which offers many recreational... View all property information
    Location Information
    Lakeville, Connecticut 06068
    5 of 5 bubbles Reviewed 26 May 2014
    My friends and I stayed at this house for a race weekend at Lime Rock Park. The location of this house is perfect - 15 minutes from the track, walking distance from a small lake...
    5 of 5 bubbles Reviewed 6 May 2014
    We rented this sweet home in Lakeville for the bride and bridesmaids for my son's wedding. The bridal party came from far and wide and this was the perfect destination for the...
    See all reviews
    1 / 27
    3.5 of 5 bubbles (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 bubbles 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...
    See all reviews
    1 / 14
    5 of 5 bubbles (1) Excellent
    Sheffield
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the... View all property information
    Location Information
    Sheffield, Berkshires 01257
    5 of 5 bubbles Reviewed 28 October 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
    See all reviews
    1 / 24
    5 of 5 bubbles (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 22
    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
    Location Information
    Otis, Berkshires 01255
    1 / 19
    5 of 5 bubbles (1) Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect... View all property information
    Location Information
    North Egremont, Berkshires 01230
    5 of 5 bubbles Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
    See all reviews
    1 / 7
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 23
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    PRIVACY-QUIET- HIKE-SKI-RELAX FYI in the winter, a huge hill behind the house on our property is fantastic for sledding . Animals you might see- Turkeys, Ducks, Bobcat, Bear, Deer, Otter, Muskrat, Heron depending on the season. A 1/4 mile driveway thru the woods takes you to 38 acres, and this... View all property information
    Location Information
    Stockbridge, Berkshires 01260
    1 / 17
    5 of 5 bubbles (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Internet Access
    • Parking
    • Mountain Views
    • Hot Tub
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 11 October 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    5 of 5 bubbles 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...
    See all reviews
    1 / 12
    5 of 5 bubbles (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 bubbles Reviewed 5 August 2016
    What a charming, relaxing, and peaceful rental in the very heart of Berkshires cultural activities and venues. The view and pool are splendid, the apartment itself is private...
    5 of 5 bubbles Reviewed 26 July 2016
    From the lawn of the cottage, one looks down on farms, meadows, and mountains. The sky is so big, I thought I was in Montana. One step out the door and you're walking on rambling...
    See all reviews
    1 / 10
    4 of 5 bubbles (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01230
    1 / 21
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining.... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 21
    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Skiing: Property Is...
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    • Grill
    • Central Heating
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
    Location Information
    Monterey, Berkshires 01245
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 11
    5 of 5 bubbles (18) Excellent
    Falls Village, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Balcony
    • Grill
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
    Location Information
    Falls Village, Connecticut 06031
    4 of 5 bubbles Reviewed 14 September 2016
    Enjoyed our stay at this beautiful, well appointed cottage and would book again. Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
    5 of 5 bubbles Reviewed 3 September 2016
    We spent a very relaxing weekend here and took great advantage of the deck overlooking the river. Everything was as described and depicted in photos. It was awesome to hear the...
    See all reviews
    1 / 24
    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Terrace
    • Balcony
    • Washer
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 10
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the "Silo Studio", there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
    Location Information
    Tyringham, Berkshires 01264
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Private Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 7
    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Lee, Berkshires 01238
    1 / 23
    Lakeville, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    -Available Christmas and New Years -3 Ski Mountains nearby. Mohawk, Butternut, Catamount. Just steps to everything in town! Or grab a tall glass of Lemonade and a good book & relax on the porch. This petite in-town home is convenient to restaurants, shops, & Lake. The perfect spot to getaway &... View all property information
    Location Information
    Lakeville, Connecticut 06039
    1 / 11
    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore... View all property information
    Location Information
    Copake Falls, New York 12517
    1 / 8
    5 of 5 bubbles (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles 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...
    See all reviews
    1 / 46
    5 of 5 bubbles (1) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 29 May 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
    See all reviews
    1 / 37
    5 of 5 bubbles (1) Excellent
    Salisbury, CT
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
    Location Information
    Salisbury, Connecticut 06079
    5 of 5 bubbles Reviewed 7 September 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our pace...
    See all reviews
    1 / 9
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Tyringham, Berkshires 01264
    1 / 24
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the... View all property information
    Location Information
    Monterey, Berkshires 01245
    1 / 19
    5 of 5 bubbles (4) Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed 2 September 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences from...
    5 of 5 bubbles Reviewed 1 September 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
    See all reviews