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Elder Access Vacation Rentals in Berkshires

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From
$580
Per Night
1 / 23
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Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$290
Per Night
1 / 10
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Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 5
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$168
Per Night
1 / 16
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Hancock
1 Bedroom, 1 Bathroom, Sleeps 6
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$139
Per Night
1 / 10
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North Adams
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Deck
  • Ceiling Fans
  • VCR
  • Patio
  • Refrigerator
  • DVD Player
  • TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
I have a 2 to 3 bedroom first floor apartment. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! Animals are welcome... I have a cat that I usually keep there... The master bedroom has an extended queen sleep number bed and the spare... View all property information
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5 of 5 stars Reviewed 6 July 2014
Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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$208
Per Night
1 / 16
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Sauna
  • DVD Player
  • Dishwasher
  • Refrigerator
  • Hot Tub
  • Dryer
  • Satellite TV
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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 25 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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$151
Per Night
1 / 8
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Hinsdale
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • DVD Player
  • Dishwasher
  • TV
  • Parking
  • Ceiling Fans
  • Deck
  • VCR
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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$579
Per Night
1 / 32
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Stockbridge
4 Bedrooms, 4 Bathrooms, Sleeps 12
Bookings
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Amenities & Details
  • TV
  • Dishwasher
  • Safe
  • Garage
  • DVD Player
  • Microwave
  • Sauna
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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5 of 5 stars Reviewed 3 December 2014
What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
5 of 5 stars Reviewed 18 July 2014
Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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$133
Per Night
1 / 35
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Charlemont
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Washer
  • Microwave
  • Dryer
  • Stereo System
  • Air Conditioning
  • Garage
  • Deck
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening... View all property information
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5 of 5 stars Reviewed 26 November 2014
Cavalier Cottage is a gem for people and dogs. My family and I were impressed by the amount of detail put into it---- it had everything you can think of- gourmet tea and...
5 of 5 stars Reviewed 18 November 2014
The Cavalier Cottage is a nice, clean and bright studio cottage. Pat is the perfect host, providing us with warm scones and orange juice every morning. She welcomed us and our 2...
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From
$319
Per Night
1 / 32
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Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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5 of 5 stars Reviewed 29 August 2014
This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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$290
Per Night
1 / 12
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West Stockbridge
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
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Amenities & Details
  • Patio
  • Microwave
  • TV
  • Dryer
  • Deck
  • DVD Player
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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5 of 5 stars Reviewed 28 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 31 August 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
$290
Per Night
1 / 16
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North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Grill
  • Ceiling Fans
  • Refrigerator
  • Dishwasher
  • Deck
  • Waterfront
  • VCR
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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5 of 5 stars Reviewed 16 August 2014
The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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From
$266
Per Night
1 / 4
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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Amenities & Details
  • Refrigerator
  • Safe
  • DVD Player
  • Washer
  • Parking
  • Dryer
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 11 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
$696
Per Night
1 / 33
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Great Barrington
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Fireplace
  • Washer
  • Microwave
  • Refrigerator
  • TV
  • Parking
  • Patio
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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From
$232
Per Night
1 / 11
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Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Grill
  • Fireplace
  • Washer
  • Ceiling Fans
  • Dishwasher
  • Parking
  • Dryer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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3 of 5 stars Reviewed 30 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
$58
Per Night
1 / 6
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Monterey
1 Bedroom, 1 Bathroom, Sleeps 1
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We rent our house for a full winter season from November through March. You can enjoy all holidays, school breaks, weekends during the winter in your own winter wonderland. Contact us for all details. Walk to charming 200 year old Monterey with library, playground, playing fields, ice skating... View all property information
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From
$580
Per Night
1 / 18
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Hinsdale
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Grill
  • Dryer
  • Microwave
  • Parking
  • Hot Tub
  • Refrigerator
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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From
$182
Per Night
1 / 9
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 1
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
$209
Per Night
1 / 15
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Sandisfield
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year... View all property information
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From
$464
Per Night
1 / 24
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Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • Ceiling Fans
  • Hot Tub
  • Microwave
  • Sauna
  • Gym
  • Fireplace
  • TV
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
$261
Per Night
1 / 16
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Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Microwave
  • Parking
  • DVD Player
  • Grill
  • Dishwasher
  • Sauna
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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
$151
Per Night
1 / 16
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Stockbridge
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Waterfront
  • Highchair
  • Microwave
  • Internet Access
  • Patio
  • Satellite TV
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
New Listing on Tripadvisor. One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center.... View all property information
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From
$261
Per Night
1 / 21
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Lee
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Dryer
  • Washer
  • Parking
  • Refrigerator
  • Patio
  • Microwave
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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From
$667
Per Night
1 / 5
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Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
$290
Per Night
1 / 5
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Granville
5 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The house has a unique setting in the heart of a nature... View all property information
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From
$281
Per Night
1 / 15
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Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Ceiling Fans
  • Fireplace
  • Grill
  • Deck
  • Dishwasher
  • Refrigerator
  • Microwave
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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
$203
Per Night
1 / 4
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South Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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From
$290
Per Night
1 / 14
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Lenox
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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From
$348
Per Night
1 / 29
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Monterey
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Patio
  • Grill
  • Washer
  • Parking
  • Gym
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The house is a lovely pre revolutionary war house with 3 large fire places set in the woods on 16 acres. It is a half mile from Lake Garfield in the Berkshires, 10 miles from Tanglewood in Stockbridge. The house has 3 plus bedrooms, 2 studies, kitchen, dining room,, three fire places, two living... View all property information
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From
$155
Per Night
1 / 13
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Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Sauna
  • Ceiling Fans
  • DVD Player
  • Dishwasher
  • Refrigerator
  • Gym
  • Fireplace
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses. View all property information
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From
$232
Per Night
1 / 11
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Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Microwave
  • DVD Player
  • TV
  • Refrigerator
  • Linens Provided
  • Hairdryer
  • Paper Towels...
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Recently renovated it... View all property information
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From
$870
Per Night
1 / 7
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Lee
5 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
--Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,... View all property information
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From
$696
Per Night
1 / 15
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Tyringham
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • Porch
  • Microwave
  • Refrigerator
  • Washer
  • Dishwasher
  • DVD Player
  • Satellite TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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From
$348
Per Night
1 / 11
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Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
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Amenities & Details
  • Garage
  • Microwave
  • Ceiling Fans
  • Dishwasher
  • Hot Tub
  • Refrigerator
  • Parking
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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From
$348
Per Night
1 / 23
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Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Fireplace
  • Garage
  • Washer
  • Dryer
  • DVD Player
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace;... View all property information
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From
$435
Per Night
1 / 5
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Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Ceiling Fans
  • Microwave
  • Dishwasher
  • Parking
  • Gym
  • Hot Tub
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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From
$232
Per Night
1 / 12
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Lee
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
  • Air Conditioning
  • Hairdryer
  • TV
  • Fireplace
  • Porch
  • Parking
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
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From
$290
Per Night
1 / 21
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Monterey
5 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • Dishwasher
  • Washer
  • Refrigerator
  • Patio
  • Dryer
  • DVD Player
  • Ceiling Fans
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$203
Per Night
1 / 12
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Windsor
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you... View all property information
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From
$261
Per Night
1 / 10
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Great Barrington
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (12) Make Enquiry
Amenities & Details
  • Hairdryer
  • Refrigerator
  • Central Heating
  • Microwave
  • Parking
  • DVD Player
  • Grill
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
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5 of 5 stars Reviewed 17 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 22 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
$226
Per Night
1 / 11
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New Ashford
4 Bedrooms, 3 Bathrooms, Sleeps 7
Details Reviews (14) Make Enquiry
Amenities & Details
  • Safe
  • Satellite TV
  • Dishwasher
  • Fireplace
  • Microwave
  • Grill
  • Refrigerator
  • Terrace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England’s finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas... View all property information
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5 of 5 stars Reviewed 1 December 2014
The house was everything we expected. Right from the beginning there was clear communication between us, the owner and the property manager. The booking process was easy. Checking...
5 of 5 stars Reviewed 10 November 2014
Stayed at the house for 5 days at the end of October, after a recommendation by a good friend. The house & surrounding area have a lot of history. Every morning I visited the...
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From
$174
Per Night
1 / 13
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Florida
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (2) Make Enquiry
Amenities & Details
  • Gym
  • Microwave
  • Refrigerator
  • DVD Player
  • Playground
  • Stereo System
  • Deck
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
50 acre mountain top property in the Berkshires located between North Adams and Charlemont, Massachusetts with mountain views and within close proximity to all kinds of outdoor recreational opportunities including beaches, swimming, whitewater rafting and kayaking, hunting and fishing, hiking and... View all property information
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5 of 5 stars Reviewed 1 July 2014
Great apartment (one floor of a cabin) to rent. Stayed very cool and comfortable and had comfortable rooms. Bathroom was quite big and was stocked with more than enough...
5 of 5 stars Reviewed 1 November 2013
What could be better than a private apartment on top of a mountain in the fall in western Massachusetts with french doors open to the sunrise? Margot is a most gracious and...
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$115
Per Night
1 / 19
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (22) Make Enquiry
Amenities & Details
  • Safe
  • Grill
  • DVD Player
  • Deck
  • Patio
  • Microwave
  • Air Conditioning
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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 4 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 20 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
$116
Per Night
1 / 8
Pittsfield
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Refrigerator
  • Deck
  • Washer
  • Satellite TV
  • Microwave
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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5 of 5 stars Reviewed 3 July 2013
WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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$348
Per Night
1 / 18
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Enquiry
Amenities & Details
  • TV
  • VCR
  • Dishwasher
  • Sauna
  • Refrigerator
  • Dryer
  • Washer
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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 1 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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$174
Per Night
1 / 13
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Monterey
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (13) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • DVD Player
  • Playground
  • Garage
  • Washer
  • Refrigerator
  • Dishwasher
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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From
$226
Per Night
1 / 29
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North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Enquiry
Amenities & Details
  • Playground
  • Ceiling Fans
  • Fireplace
  • DVD Player
  • TV
  • Deck
  • Gym
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the... View all property information
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5 of 5 stars Reviewed 24 August 2014
I booked the Rose & Goat Retreat for my sister's Bachelorette Weekend in the Berkshires! Not only was it the perfect location because it was only 11 miles away from our zip lining...
5 of 5 stars Reviewed 13 March 2014
This place is an absolutely gorgeous lodge, with an incredible view of the Berkshires. Margo was very hospitable and took great care of all of our needs. The pictures don't do...
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$348
Per Night
1 / 16
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Becket
3 Bedrooms, 4 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • DVD Player
  • Dryer
  • Refrigerator
  • Fireplace
  • Garage
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
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From
$290
Per Night
1 / 19
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Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Patio
  • Washer
  • Grill
  • DVD Player
  • Dryer
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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From
$501
Per Night
1 / 8
Payment Protection
Charlemont
5 Bedrooms, 3 Bathrooms, Sleeps 14
Booking
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Garage
  • Water Views
  • Refrigerator
  • TV
  • Parking
  • Microwave
  • Central Heating
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
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From
$348
Per Night
1 / 9
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Housatonic
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Stereo System
  • Dishwasher
  • Washer
  • DVD Player
  • Dryer
  • Satellite TV
  • Porch
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This house is a perfect family retreat in the Berkshires. Nestled in the Village of Housatonic you will be centrally located to all Berkshire attractions. Less that ten minutes from skiing and Tanglewood, as well as the shops and restaurants of Stockbridge, Lenox, and Great Barrington, this is... View all property information
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