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Holiday Homes and Apartments East Chatham, NY and nearby

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All 66 Rentals in the East Chatham Area
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From
$370
Per Night
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1 / 9
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East Chatham
3 Bedrooms, 3 Bathrooms, Sleeps 6
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From
$369
Per Night
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1 / 6
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East Chatham
5 Bedrooms, 3 Bathrooms, Sleeps 15
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The following rentals are within 25 kilometres of East Chatham, New York.

From
$89
Per Night
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1 / 27
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$278
Per Night
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1 / 14
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Hancock, MA
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy... View all property information
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From
$179
Per Night
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1 / 16
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Hancock, MA
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
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5 of 5 stars Reviewed 17 October 2014
This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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From
$247
Per Night
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1 / 18
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Austerlitz
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes... View all property information
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From
$300
Per Night
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1 / 9
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Valatie
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Stunning New Lakefront Home Near Berkshires with Gourmet Kitchen, large expansive views of Kinderhook Lake. All the bells and whistles including a TV in the Master Bathroom and a whole house stereo system. This home is an air conditioned, upscale Craftsman- styled cottage with 75 feet of lakefront... View all property information
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From
$308
Per Night
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1 / 10
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Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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5 of 5 stars Reviewed 21 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
$432
Per Night
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1 / 9
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Great Barrington, MA
5 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
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Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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From
$167
Per Night
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1 / 11
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Richmond, MA
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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From
$617
Per Night
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1 / 23
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Stockbridge, MA
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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From
$185
Per Night
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1 / 14
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Ghent
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a park-like property it's a beautiful place to vacation. You also have access to a very large swimming pool and the large wooden decks of the main house. The... View all property information
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5 of 5 stars Reviewed 7 August 2013
This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads full...
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From
$370
Per Night
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1 / 12
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 1
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • x
About this property
Wyndham Bentley Brook Ski-In Ski Out Wyndham Bentley Brook Resort Ski-In Ski-Out at Jiminy Peak at Wyndham Bentley Brook Resort. Beginners or Experts, we have -programs designed for all levels. After a couple days of skiing, you want to venture out and hit local attractions like, Barrington... View all property information
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4 of 5 stars Reviewed 21 July 2014
The condo was great - clean, roomy, stocked with expected items (towels, linens, shampoos, etc.) - my kids felt that it was very hotel-like. Location was perfect for us, although...
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From
$154
Per Night
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1 / 6
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West Stockbridge, MA
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • 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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5 of 5 stars Reviewed 19 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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From
$308
Per Night
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1 / 16
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Columbiaville
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Complete renovation with privacy. This rural mill worker's cottage has been upgraded with midcentury touches while leaving antique finishes. Overlooking the Kinderhook Creek rapids on a private paved road. Minutes to Hudson and Kinderhook, NY. This 1400 sf home is on three levels with laundry in... View all property information
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From
$615
Per Night
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1 / 32
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Stockbridge, MA
4 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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5 of 5 stars Reviewed 4 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 19 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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From
$278
Per Night
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1 / 16
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Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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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...
5 of 5 stars Reviewed 1 October 2013
We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
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From
$185
Per Night
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1 / 21
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Lenox, MA
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (18) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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5 of 5 stars Reviewed 22 October 2014
We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
4 of 5 stars Reviewed 21 October 2014
I visited Lenox on a girls leaf peeping trip in mid-October. We found this house to be cozy & warm. It is very quaint & centrally located. It was nice to have most of the comforts...
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From
$228
Per Night
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1 / 12
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Alford, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • 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... View all property information
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From
$617
Per Night
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1 / 11
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Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • 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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From
$278
Per Night
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1 / 10
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Great Barrington, MA
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (12) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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5 of 5 stars Reviewed 18 August 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed 23 July 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
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From
$740
Per Night
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1 / 33
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Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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From
$308
Per Night
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1 / 17
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West Stockbridge, MA
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Details Reviews (8) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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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5 of 5 stars Reviewed 29 October 2014
Our group of 9 friends stayed here for two nights in late October. Everyone was pleased with the accomodations. The house is close to Stockbridge, Lee, and Lenox. It is nestled in...
5 of 5 stars Reviewed 1 September 2014
We were a group nine. We found the house to have a rustic charm complete with hardwood floors and exposed beams in the walls and ceilings. We tended to congregate in the living...
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From
$221
Per Night
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1 / 16
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Sauna
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your... View all property information
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4 of 5 stars Reviewed 26 October 2014
Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small...
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From
$194
Per Night
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1 / 9
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 1
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc..... View all property information
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From
$282
Per Night
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1 / 4
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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4 of 5 stars Reviewed 12 August 2013
Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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From
$185
Per Night
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1 / 16
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Stephentown
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful three bed room home with a private master bedroom with attached bath and deck. Two bedrooms downstairs with a shared bathroom. Modern Kitchen with everything you need to make wonderful meals, Large deck out the back with tables, chairs and gas grill. House has a spacious living room with... View all property information
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4 of 5 stars Reviewed 30 October 2014
Beautiful home, comfortable BUT there were no sheets on the bed. And when I contacted the owner nothing was done about it. Kitchen was outfitted with everything. There was a...
4 of 5 stars Reviewed 28 July 2014
We had a great time and would recommend this house to anyone looking for a quiet escape. The house was in great condition, with full kitchen, lots of room, carpeting, amazing...
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From
$370
Per Night
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1 / 18
Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), Alpine Slide (warmer months), Berkshire Express Chairlift to Summit Lodge during ski season. The Berkshire Express provides scenic rides during warmer months. Bentley Brook is situated Slope Side for SKI/IN - SKI/OUT all winter... View all property information
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5 of 5 stars Reviewed 2 August 2013
Really nice accommodations & the staff was amazing, going out of their way to help in any way possible. Easy access to Jiminy Peak, which was full of activities for the...
5 of 5 stars Reviewed 31 January 2013
We spent time at Bentley Brook with "Kids" and the "Grands". Loved the 2BR, 2B with full K and really nice LR. Immaculate, extremely well equipped and spacious. The convenience...
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From
$370
Per Night
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1 / 12
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Austerlitz
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This amazing house on 16 private acres on a dirt road is 15 minutes away from the Berkshires with all its amazing cultural events and great food. Skinny dip in your own 1/2 acre private pond and bbq on a deck secluded from all other houses, then go out to a great meal, and hear the Boston Symphony... View all property information
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From
$555
Per Night
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1 / 20
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Richmond, MA
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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From
$122
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1 / 19
Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (22) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking... View all property information
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5 of 5 stars Reviewed 5 November 2014
Beautiful grounds, quiet, clean. Owner is available at all times. Close to all area attractions. Great Barrington, Stockbridge, West Stockbridge, Lennox are all within a 10 min...
5 of 5 stars Reviewed 21 July 2014
Stayed one night for weekend to Tanglewood festival. At first, it was a bit hard to find the house number accessing from north, but very close to the campus. Followed Carole's...
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From
$308
Per Night
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1 / 14
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West Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
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Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Private Fishing...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at www.aberkshirehome.com The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural... View all property information
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5 of 5 stars Reviewed 3 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 26 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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From
$574
Per Night
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1 / 27
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Great Barrington, MA
5 Bedrooms, 3 Bathrooms, Sleeps 10
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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3 of 5 stars Reviewed 12 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...
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$247
Per Night
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1 / 11
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Stockbridge, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
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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3 of 5 stars Reviewed 31 July 2014
Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
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From
$802
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1 / 22
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Great Barrington, MA
4 Bedrooms, 6 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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From
$173
Per Night
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1 / 7
Richmond, MA
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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2 of 5 stars Reviewed 11 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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From
$298
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1 / 15
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Lenox, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close... View all property information
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From
$247
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1 / 24
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Stockbridge, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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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From
$197
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1 / 7
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Stephentown
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dryer
  • Grill
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Perfect weekend retreat or short term furnished rental close to all Berkshire, MA amenities and Jiminy Peak Mountain Resort, museums, theatre, restaurants, shopping and more! 20 Minutes to Williamstown, 25 to Pittsfield, 30 to Albany. Home is efficient easily maintained in an adorable 1870's... View all property information
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From
$278
Per Night
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1 / 16
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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From
$493
Per Night
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1 / 24
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Lenox, MA
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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From
$709
Per Night
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1 / 5
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Stockbridge, MA
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Private setting on over three acres, this artist designed and newly renovated home has cathedral ceilings in all rooms. It features a luxurious and spacious master bedroom suite with jacuzzi tub & outdoor shower Skylights are everywhere and designed to let in the light and mountain views from... View all property information
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From
$141
Per Night
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1 / 10
Chatham
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Spend some time in this charming cottage with spectacular views overlooking the Hudson Valley in upstate New York. Secluded, yet only a short drive to the Berkshires, where music, theater, history, and natural beauty abound! Spend Spring, Summer or Fall surrounded by over 100 private acres of... View all property information
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From
$370
Per Night
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1 / 11
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Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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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1 / 7
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Hancock, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save. View all property information
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From
$247
Per Night
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1 / 10
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Great Barrington, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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!)... View all property information
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From
$308
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1 / 19
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Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
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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From
$740
Per Night
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1 / 4
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Stephentown
4 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,... View all property information
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From
$308
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1 / 7
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Lenox, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This cozy cottage located in the heart of the Berkshires is located just 5 minutes fom Tanglewood, Shakespeare and Company, Lenox center, and Stockbridge bowl. If the wind is blowing in the right direction, you can hear the Boston Symphony rehearsing. My home was built in the 1940s, and offers all... View all property information
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From
$308
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1 / 14
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Lenox, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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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