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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
Studio, 2 beds, 1 shared bathroom
7–12 Sept
,
4.96 out of 5 average rating, 305 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.93 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
4.98 out of 5 average rating, 64 reviews, 3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
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
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4.94 out of 5 average rating, 47 reviews, 4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
Flat in Stockbridge
Historic Retreat
4.86 out of 5 average rating, 59 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.95 out of 5 average rating, 184 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Sept
Top guest favourite
Home in Lee
GreenHouse
4.99 out of 5 average rating, 133 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Oct
Home in Stockbridge
Light Filled - Modern Rustic Home
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
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 Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
4.89 out of 5 average rating, 170 reviews, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4.88 out of 5 average rating, 50 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
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.84 out of 5 average rating, 154 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
Home in Stockbridge
Bramaluna
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug