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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 bed, 1 private bathroom
5–10 Sept
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4.96 out of 5 average rating, 122 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.92 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.95 out of 5 average rating, 183 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Sept
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
4.93 out of 5 average rating, 44 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
4.83 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4.99 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Home in Stockbridge
Light-filled Carpenter's Cottage
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
5.0 out of 5 average rating, 21 reviews, 4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
4.96 out of 5 average rating, 26 reviews, 5 bedrooms, 8 beds, 2.5 bathrooms
23–28 Aug
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
4.96 out of 5 average rating, 301 reviews, 2 beds, 1 bathroom
7–12 Sept
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4.84 out of 5 average rating, 87 reviews, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4.91 out of 5 average rating, 46 reviews, 4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Flat in Stockbridge
Three bedroom duplex in Stockbridge on the river
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
Flat in Pittsfield
Mid-Berkshires
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
4.98 out of 5 average rating, 63 reviews, 3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept