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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
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds
13–18 Sept
4.95 out of 5 average rating, 183 reviews
Flat in Pittsfield
Mid-Berkshires
2 bedrooms, 2 beds
22–27 Aug
New place to stay
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds
24–29 Aug
4.95 out of 5 average rating, 43 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
2–7 Aug
4.92 out of 5 average rating, 92 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds
2–7 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
4 bedrooms, 5 beds
1–6 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 132 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.83 out of 5 average rating, 6 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Lee
Stylish Mid-century Modern Berkshires Cape
4 bedrooms, 5 beds
18–23 Jul
4.97 out of 5 average rating, 136 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed
19–24 Jul
4.89 out of 5 average rating, 168 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
2–7 Aug
4.99 out of 5 average rating, 92 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed
23–28 Aug
4.84 out of 5 average rating, 152 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
18–23 Sept
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds
7–12 Sept
4.91 out of 5 average rating, 45 reviews