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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 beds, 2.5 private bathrooms
13–18 Sept
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4.95 out of 5 average rating, 183 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 92 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 170 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 255 reviews
Guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.93 out of 5 average rating, 44 reviews
Guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Oct
4.99 out of 5 average rating, 132 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
5–10 Sept
4.96 out of 5 average rating, 122 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 302 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
26–31 Jul
4.83 out of 5 average rating, 24 reviews
Top guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 317 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 47 reviews