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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 Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
8–13 Sept
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, 90 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, 310 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 343 reviews, 1 bedroom, 1 bed, 2 bathrooms
7–12 Sept
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4.91 out of 5 average rating, 44 reviews, 4 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
Superhost
Home in Stockbridge
Mac Shores | 5 min to Tanglewood ! • Shared Beach
4.81 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 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
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 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
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
12–17 Jul
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
Top guest favourite
Home in Lee
Stylish Berkshires Retreat
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
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
Home in Stockbridge
Your Stockbridge Getaway
4.96 out of 5 average rating, 25 reviews, 5 bedrooms, 8 beds, 2.5 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
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
4.89 out of 5 average rating, 246 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
4.89 out of 5 average rating, 61 reviews, 1 bed, 1 bathroom
12–17 Jul