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Holiday Rentals and Homes in West Stockbridge, MA

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    All 22 Rentals in the West Stockbridge Area
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    €115
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    €230
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    1 / 19
    5 of 5 stars (12) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    travellers have booked this property
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    €230
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    The following rentals are within 10 kilometers of West Stockbridge, Massachusetts.

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    €124
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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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    €207
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    1 / 16
    5 of 5 stars (4) Excellent
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • 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
    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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    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...
    5 of 5 stars Reviewed 30 September 2013
    We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
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    €460
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    5 of 5 stars Reviewed 4 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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    €461
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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) 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
    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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    €138
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
    Overview Reviews (19) Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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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    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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    €184
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    1 / 11
    3 of 5 stars (1) Average
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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    3 of 5 stars Reviewed 31 July 2014
    Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
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    €369
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    1 / 12
    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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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    From
    €461
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    1 / 11
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • 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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    From
    €120
    / Night
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    1 / 16
    Stockbridge
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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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    €530
    / Night
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    1 / 5
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Private setting on over three acres, this artist designed and newly renovated home has cathedral ceilings in all rooms. It features a luxurious and spacious master bedroom suite with jacuzzi tub & outdoor shower Skylights are everywhere and designed to let in the light and mountain views from... View all property information
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    From
    €415
    / Night
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    1 / 20
    Richmond
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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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    €369
    / Night
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    1 / 24
    Lenox
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    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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    €223
    / Night
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    1 / 15
    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close... View all property information
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    €230
    / Night
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    1 / 14
    Lenox
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows... View all property information
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    From
    €184
    / Night
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    1 / 24
    Stockbridge
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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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    €91
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    1 / 19
    4.5 of 5 stars (22) Very good
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking... View all property information
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    5 of 5 stars Reviewed 5 November 2014
    Beautiful grounds, quiet, clean. Owner is available at all times. Close to all area attractions. Great Barrington, Stockbridge, West Stockbridge, Lennox are all within a 10 min...
    5 of 5 stars Reviewed 20 July 2014
    Stayed one night for weekend to Tanglewood festival. At first, it was a bit hard to find the house number accessing from north, but very close to the campus. Followed Carole's...
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    €230
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    1 / 13
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview 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
    • x
    • Wheelchair access
    • 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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    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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    €129
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    1 / 7
    2 of 5 stars (1) Poor
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 7
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Berkshires, in Western Massachusetts, are known as center of cultural activities, including but not limited to Tanglewood (the summer home of the Boston Symphony Orchestra), Shakespeare Theatre Festival, Jacobs Pillow, Williamstown Theatre Festival, plus numerous recreational opportunities for... View all property information
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    2 of 5 stars Reviewed 11 September 2014
    I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The...
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    €230
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    1 / 10
    Richmond
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • 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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