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Holiday Rentals and Homes in Housatonic, MA

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    The following rentals are within 10 kilometers of Housatonic, Massachusetts.

    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 25
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    5 of 5 bubbles (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 2 weeks ago
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    1 / 30
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 23 October 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    1 / 10
    5 of 5 bubbles (1) Excellent
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 18 October 2016
    We had a wonderful time staying at this property. The house is full of charming details - we kept discovering art objects till the time of our departure. The kids had fun using...
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    1 / 32
    5 of 5 bubbles (4) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 9 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
    5 of 5 bubbles Reviewed 25 October 2016
    We visited Stockbridge with a bunch of friends during the Fall. The house is beautiful, very clean, and well-stocked with anything we could have needed. They even had toys and...
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    1 / 20
    5 of 5 bubbles (26) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    4 of 5 bubbles Reviewed 2 weeks ago
    This Berkshire Farmhouse worked out great for our 3 family reunion. The house was clean, stocked with plenty of blankets and towels, as well as many other amenities. The owner...
    5 of 5 bubbles Reviewed 9 May 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    PRIVACY-QUIET- HIKE-SKI-RELAX FYI in the winter, a huge hill behind the house on our property is fantastic for sledding . Animals you might see- Turkeys, Ducks, Bobcat, Bear, Deer, Otter, Muskrat, Heron depending on the season. A 1/4 mile driveway thru the woods takes you to 38 acres, and this... View all property information
    Location Information
    Stockbridge, Berkshires 01260
    1 / 12
    5 of 5 bubbles (4) Excellent
    Alford
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural... View all property information
    Location Information
    Alford, Berkshires 01266
    5 of 5 bubbles Reviewed 16 October 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked goods...
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    1 / 11
    3.5 of 5 bubbles (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 bubbles Reviewed 21 July 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 bubbles Reviewed 14 July 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    1 / 8
    5 of 5 bubbles (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Parking
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    1 / 20
    5 of 5 bubbles (6) Excellent
    West Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed 27 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
    5 of 5 bubbles Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
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    1 / 27
    3.5 of 5 bubbles (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Grill
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    3 of 5 bubbles Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    1 / 12
    5 of 5 bubbles (21) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Parking
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 bubbles Reviewed 5 August 2016
    What a charming, relaxing, and peaceful rental in the very heart of Berkshires cultural activities and venues. The view and pool are splendid, the apartment itself is private...
    5 of 5 bubbles Reviewed 26 July 2016
    From the lawn of the cottage, one looks down on farms, meadows, and mountains. The sky is so big, I thought I was in Montana. One step out the door and you're walking on rambling...
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    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Mountain Views
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 14
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Patio
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Elegant, contemporary one bedroom house sleeps 4. Great central location. Peace, beauty and convenience. Perfectly located for all Berkshires activities, while still maintaining privacy and quiet. All new construction. This is my mother-in-law's property (I handle her online reservations) and... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 21
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining.... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 22
    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Great Barrington, Berkshires 01236
    1 / 15
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • Balcony
    • Housekeeping...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master... View all property information
    Location Information
    Great Barrington, Berkshires 01230
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    1 / 20
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique... View all property information
    Location Information
    Stockbridge, Berkshires 01236
    1 / 10
    4 of 5 bubbles (1) Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
    Location Information
    Great Barrington, Berkshires 01230
    1 / 25
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 6,700 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Great Barrington, Berkshires 01230
    1 / 22
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air... View all property information
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    Stockbridge, Berkshires 01262
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Garden
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
    • Private Garden
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 18
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Parking
    • Satellite TV
    • Balcony
    • Air Conditioning
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    • DVD Player
    • Washer
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey.... View all property information
    Location Information
    Great Barrington, Berkshires
    1 / 30
    5 of 5 bubbles (3) Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making each room flow into another.... View all property information
    Location Information
    Great Barrington, Berkshires 01230