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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
4–9 Jul
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4.96 out of 5 average rating, 120 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.97 out of 5 average rating, 89 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 308 reviews, 3 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.84 out of 5 average rating, 148 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Lee
GreenHouse
4.99 out of 5 average rating, 131 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Oct
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 179 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 40 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Sept
Guest favourite
Home in Lee
Stylish Berkshires Retreat
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4.9 out of 5 average rating, 42 reviews, 4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
4.89 out of 5 average rating, 245 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4.93 out of 5 average rating, 45 reviews, 4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Jul
Home in Lenox
Walk to Tanglewood from new 2BR Berkshire home!
New place to stay, 2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 310 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Sept
Loft in Lee
Waterfront Berkshires Studio w/ Dock on Goose Pond
New place to stay, 1 bed, 1 bathroom
11–16 Jul
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Lenox
Cozy Home in Lenox
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Jul