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Vacation Rentals in West Stockbridge, MA and nearby

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    $330
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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
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    $396
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    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Ping Pong Table
    • Satellite TV
    • Wi-Fi
    • Game Room
    • Swingset
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    West Stockbridge, Berkshires 01266
    From
    $198
    / Night
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    West Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Central Heating
    • Horse Riding Nearby
    • Watersports Nearby
    • Refrigerator
    • Wi-Fi
    • Patio
    • There Are Tennis...
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
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    Location Information
    West Stockbridge, Berkshires 12029

    The following rentals are within 10 kilometres of West Stockbridge, Massachusetts.

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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12
    other travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Sauna
    • Mountain Views
    • DVD Player
    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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    Location Information
    Stockbridge, Berkshires 01262
    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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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • TV
    • Refrigerator
    • Wi-Fi
    • Waterfront
    • Cooker
    • Linens Provided
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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. Self contained and private. You... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 13 July 2015
    I just got back from my weekend stay here last night, and if I hadn't been so tired, I would have posted this review already! I was absolutely thrilled with this rental - where...
    4 of 5 stars Reviewed 21 June 2015
    Lovely home, great location, walking distance to the town of Stockbridge. Many things to see and do while we stayed for our five day trip. Must see: Naumkeg, Shrine of Divine...
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7
    other travellers have booked this property
    Overview Reviews (19) Make Enquiry
    Overview Reviews (19)
    Amenities & Details
    • Dryer
    • Stereo System
    • Grill
    • Internet Access
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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    Lenox, Berkshires 01240
    5 of 5 stars Reviewed 3 January 2015
    Ski trip in Berkshires and this place was perfect. Gave us nice options to do on off days. Debra was great with any issues that came up and was very helpful and responsive...
    5 of 5 stars Reviewed 22 October 2014
    We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
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    $172
    / Night
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Horse Riding Nearby
    • Washer
    • Central Heating
    • Dryer
    • Cooker
    • Housekeeping...
    • Wi-Fi
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    From
    $297
    / Night
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Fireplace
    • TV
    • Stereo System
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Overview Reviews (5)
    Amenities & Details
    • Boat Available
    • There Are Tennis...
    • Watersports Nearby
    • Fireplace
    • Satellite TV
    • Washer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    4 of 5 stars Reviewed 24 October 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    $528
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    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    other traveller has booked this property
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Playground
    • Shared Indoor Pool
    • Mountain Views
    • Shared Tennis Court
    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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    Location Information
    Lenox, Berkshires 01240
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    $198
    / Night
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Washer
    • Satellite TV
    • DVD Player
    • Internet Access
    • Playground
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    Location Information
    Richmond, Berkshires 01254
    From
    $297
    / Night
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Stereo System
    • Central Heating
    • Internet Access
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Waterfront
    • Water Views
    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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    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars 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...
    3 of 5 stars Reviewed 4 July 2015
    On the water with canoes, close to Tanglewood, but tired amenities. Poor second bedroom, not yet cleaned until after we arrived, but most unfortunate it was a very hot weekend...
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    $330
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    1 / 12
    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveller has booked this property
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Playground
    • Stereo System
    • Mountain Views
    • DVD Player
    • TV
    • Internet Access
    • Deck
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    Location Information
    Lenox, Berkshires 01240
    4 of 5 stars Reviewed 8 July 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    $330
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Enquiry
    Overview
    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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    Location Information
    Lenox, Berkshires 01240
    From
    $429
    / Night
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    1 / 10
    Richmond
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    In 1832, Josiah Loomis bought a parcel of land 'and the structures thereon', along what was then known as 'Massachusetts Turnpike No. 10,' the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $660
    / Night
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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Water Views
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Location Information
    Stockbridge, Berkshires 01260
    From
    $660
    / Night
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    From
    $594
    / Night
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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Fireplace
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed... View all property information
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    Location Information
    Richmond, Berkshires 01254
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    $263
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    1 / 19
    4.5 of 5 stars (27) Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (27) Make Enquiry
    Overview Reviews (27)
    Amenities & Details
    • Satellite TV
    • Patio
    • Mountain Views
    • Deck
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    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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    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed 13 August 2015
      Want to feel like you have been invited to stay with an old - or new - friend in a special part of the Berkshires, then this is the place for you. Only 4 mi...
    3 of 5 stars Reviewed 10 August 2015
    Beautiful location with lovely outdoor space! Antique Suite has spacious rooms and a very comfortable bed. Hostess made every effort to see that we enjoyed our stay, inquiring...
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    $396
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    1 / 9
    1 of 5 stars (1) Terrible
    Housatonic
    4 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Central Heating
    • Stereo System
    • Dryer
    • Refrigerator
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    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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    Location Information
    Housatonic, Berkshires 01236
    1 of 5 stars Reviewed 14 August 2015
    After our initial rental fell through due to water damage at the last minute before we left Florida for the Berkshires, we found this rental and took it. We have a dog and there...
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    $330
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    1 / 13
    5 of 5 stars (2) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Stereo System
    • Washer
    • Air Conditioning
    • Satellite TV
    • Fireplace
    • DVD Player
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed 26 May 2015
    This home is beautiful! It is an older home, and comes with the charm and quirks, which make it even more lovely! The décor is modern, simple and fits the house wonderfully. The...
    5 of 5 stars Reviewed 22 January 2015
    This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night. The surrounding...
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    $528
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    1 / 9
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dryer
    • Internet Access
    • Air Conditioning
    • Patio
    • Hot Tub
    • Satellite TV
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
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    Location Information
    Stockbridge, Berkshires
    From
    $528
    / Night
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    1 / 9
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Hot Tub
    • Dryer
    • Deck
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
    Make Enquiry
    Location Information
    Stockbridge, Berkshires