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Holiday Rentals in Sheffield, MA

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All 27 Rentals in the Sheffield Area
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From
₹31,894
Per Night
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1 / 19
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Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 15
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From
₹35,083
Per Night
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1 / 32
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Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (16) Make Enquiry

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

From
₹9,568
Per Night
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1 / 45
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Hillsdale, NY
4 Bedrooms, 3 Bathrooms, Sleeps 7
Booking
Details Reviews (2) Make Enquiry
From
₹6,379
Per Night
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1 / 8
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Hillsdale, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Indoor Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Welcome to the quiet confines of Copake Lake nestled in the heart of the Taconic Mountain Range in Columbia County, NY, bordering Massachusetts' Berkshire County. You wake up an hour past dawn, grab a cup of java and sit out on your private deck that overlooks shimmering Copake Lake, a 365 acre... View all property information
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From
₹12,758
Per Night
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1 / 14
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Copake, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to... View all property information
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5 of 5 stars Reviewed 6 February 2014
The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
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From
₹27,110
Per Night
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1 / 18
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Hillsdale, NY
3 Bedrooms, 2 Bathrooms, Sleeps 13
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • 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
Cozy modern log cabin nestled in the Berkshires in a large wooded area with landscaped yard on a small river. The cabin has a full service kitchen and a great room with dining and lounging space. There is a full entertainment center with furnished recorded music and movies. Bedrooms and bath are... View all property information
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From
₹11,801
Per Night
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1 / 12
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Alford
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
₹79,735
Per Week
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1 / 16
Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (3) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7) BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS. This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean freshwater... View all property information
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5 of 5 stars Reviewed 20 October 2014
We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really wowed...
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From
₹10,844
Per Night
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1 / 35
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North Egremont
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,... View all property information
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5 of 5 stars Reviewed 12 September 2014
I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
5 of 5 stars Reviewed 4 September 2014
Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
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From
₹12,758
Per Night
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1 / 11
Falls Village, CT
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (11) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful... View all property information
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5 of 5 stars Reviewed 21 August 2014
My sister and I stayed in the cottage for two nights this summer. It was a totally awesome experience. We were visiting the area where we had spent many wonderful summers years...
5 of 5 stars Reviewed 11 February 2014
I happened upon the cottage more or less by accident, but having stayed there twice since December, I'm confident I'll be returning again and again. The gorgeous (and very...
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From
₹9,568
Per Night
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1 / 37
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Salisbury, CT
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 17 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
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5 of 5 stars Reviewed 8 September 2014
My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our pace...
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From
₹47,841
Per Week
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1 / 4
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Copake, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the... View all property information
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From
₹11,163
Per Night
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1 / 25
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Hillsdale, NY
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two... View all property information
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5 of 5 stars Reviewed 27 October 2014
Many thanks to Bill and Eileen. We had a wonderful week and returned to the UK feeling relaxed and contented. A lovely lodge with all comforts included. Would happily stay...
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From
₹9,568
Per Night
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1 / 13
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Monterey
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (13) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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
₹31,894
Per Night
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1 / 35
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Hillsdale, NY
5 Bedrooms, 5 Bathrooms, Sleeps 14
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms... View all property information
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From
₹6,379
Per Night
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1 / 10
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Hillsdale, NY
2 Bedrooms, 1 Bathroom, Sleeps 3
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Secluded 1850s eyebrow farmhouse. Open living/dining room with original details. 2 bedrooms. 1 bath. 2 fireplaces. Large sunny stone patio. Gardens, stream, apple trees. Ten acres, surrounded by 1,000-acre Rheinstrom Hill Audubon Bird Sanctuary with miles of trails. Last house on a quiet dead-end... View all property information
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From
₹9,568
Per Night
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1 / 8
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Hillsdale, NY
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Glorious views across meadows to distant mountains. Open-plan living/dining/kitchen with fireplace, and soaring ceiling. Many glass doors lead to decks where you may drink in the view. Great master bedroom suite with state of the art bathroom, two guest rooms, family room, media room and two guest... View all property information
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From
₹19,136
Per Night
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1 / 29
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Monterey
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
₹11,482
Per Night
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1 / 15
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Sandisfield
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
₹12,758
Per Night
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1 / 10
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Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Housekeeping...
  • Mountain Views
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to... View all property information
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From
₹12,758
Per Night
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1 / 10
Copake, NY
4 Bedrooms, 3 Bathrooms, Sleeps 17
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
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From
₹19,136
Per Night
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1 / 10
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Norfolk, CT
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details 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
This newly renovated 1850's farmhouse in charming, rural Northwest CT has warmth and privacy galore! The home is located on eight acres of land on a dead end road, but is only 4 miles from the center of town! There are three bedrooms, a laundry closet, and 2 full baths upstairs. A jacuzzi... View all property information
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From
₹9,122
Per Night
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1 / 5
Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
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From
₹15,947
Per Night
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1 / 21
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Monterey
5 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Balcony
  • 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 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
₹17,031
Per Night
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1 / 5
South Egremont
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located directly on the shore of Lake Buel in Great Barrington just minutes away from Tanglewood, Jacobs Pillow and many other attractions. Our family home boasts a 40 foot screened in porch for dining and enjoying the beautiful lake. All rooms are on one floor and you can drive right up to the... View all property information
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1 / 6
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Monterey
1 Bedroom, 1 Bathroom, Sleeps 1
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
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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1 / 12
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Monterey
Studio, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. View all property information
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