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Vacation Rentals near Chesterwood Museum

4 Williamsville Rd, Stockbridge, Massachusetts 01262
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    Travelers to Stockbridge are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    23 Matching Rentals in the Stockbridge AreaView all 31 rentals
    Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)1 / 17
    (1)Excellent
    Stockbridge
    3.0 miles from Chesterwood Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    Stockbridge
    3.4 miles from Chesterwood Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge
    2.2 miles from Chesterwood Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Vacation Home1 / 32
    (5)Excellent
    Stockbridge
    1.9 miles from Chesterwood Museum
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed November 9, 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    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...
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    Location Information
    Stockbridge, Berkshires
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Stockbridge
    0.3 miles from Chesterwood Museum
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
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    Stockbridge, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Stockbridge
    2.6 miles from Chesterwood Museum
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Stockbridge, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stockbridge
    2.9 miles from Chesterwood Museum
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master...
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    Stockbridge, Berkshires
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    Stockbridge
    1.5 miles from Chesterwood Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Stockbridge, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Stockbridge
    1.6 miles from Chesterwood Museum
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Stockbridge, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stockbridge
    1.3 miles from Chesterwood Museum
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Yard
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Stockbridge, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge
    0.4 miles from Chesterwood Museum
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Yard
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **1 week minimum July & August** Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The...
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    Stockbridge, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Stockbridge
    1.3 miles from Chesterwood Museum
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Stockbridge, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge
    1.3 miles from Chesterwood Museum
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Stockbridge, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The following rentals are within 5 miles of Stockbridge.
    Enjoy Autumn in New England. Fall festivals, comfort foods, leaf peeping hikes.1 / 18
    (7)Excellent
    West Stockbridge
    4.1 miles from Chesterwood Museum
    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
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed August 27, 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...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. 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 a destination, a haven, a state...
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    West Stockbridge, Berkshires
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge
    2.9 miles from Chesterwood Museum
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed June 5, 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    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....
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    West Stockbridge, Berkshires
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge
    1.5 miles from Chesterwood Museum
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 26, 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed November 14, 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
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    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,...
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    Location Information
    West Stockbridge, Berkshires
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    West Stockbridge
    2.9 miles from Chesterwood Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lee
    4.3 miles from Chesterwood Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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!...
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    Lee, Berkshires
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    West Stockbridge
    3.2 miles from Chesterwood Museum
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 18, 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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    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...
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    Location Information
    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lee
    4.6 miles from Chesterwood Museum
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Mountain Views
    • Patio
    • Grill
    • Parking
    • Wi-Fi
    • Shared Yard
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is very rustic, literally a barn! Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot...
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    Location Information
    Lee, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lee
    3.8 miles from Chesterwood Museum
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural attractions. Live...
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    Location Information
    Lee, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    West Stockbridge
    1.6 miles from Chesterwood Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    West Stockbridge, Berkshires
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    NEW! 'Butterfly Hill' 2BR West Stockbridge House1 / 24
    (1)Excellent
    West Stockbridge
    2.5 miles from Chesterwood Museum
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Mountain Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2018
    We thoroughly enjoyed our week at Butterfly Hill. It was near Tanglewood, our main reason for the visit, and all the nearby towns where we found good restaurants and shops. We...
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    About this property
    Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provide the perfect...
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    West Stockbridge, Berkshires
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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