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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.91 out of 5 average rating, 159 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 44 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.84 out of 5 average rating, 152 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
8–13 Sept
Top guest favourite
Home in Lee
GreenHouse
4.99 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Oct
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
4.96 out of 5 average rating, 300 reviews, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
4.94 out of 5 average rating, 159 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.97 out of 5 average rating, 91 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
5.0 out of 5 average rating, 11 reviews, 3 beds, 1 bathroom
23–28 Jul
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 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
Home in West Stockbridge
Exceptional Stockbridge Retreat
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
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
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
4.89 out of 5 average rating, 167 reviews, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Home in Lee
4BDR Elegant Berkshires Escape | Beaver Creek
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
Top guest favourite
Room in Lee
Warm & Welcoming Room w/ Private Bath
4.98 out of 5 average rating, 241 reviews, 1 queen bed, 1 bathroom
4–9 Sept
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
5.0 out of 5 average rating, 29 reviews, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
4.97 out of 5 average rating, 62 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
21–26 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