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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
23–28 Aug
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4.9 out of 5 average rating, 157 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.85 out of 5 average rating, 151 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 42 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Top guest favourite
Home in Lee
GreenHouse
4.99 out of 5 average rating, 131 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Oct
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
Guest house in Stockbridge
Modern studio with views of the treetops
4.96 out of 5 average rating, 298 reviews, 2 beds, 1 bathroom
7–12 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
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
Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
4.94 out of 5 average rating, 158 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
5.0 out of 5 average rating, 28 reviews, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.96 out of 5 average rating, 180 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
4.98 out of 5 average rating, 63 reviews, 3 bedrooms, 5 beds, 2 bathrooms
2–7 Sept
Room in Stockbridge
Iris Room bright with 4 windows :)
4.32 out of 5 average rating, 41 reviews, 1 bed, 1 bathroom
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
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
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
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 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
Guest favourite
Boutique hotel in Lee
Cozy 2-bedroom apartment with WiFi, fitness room
4.93 out of 5 average rating, 41 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul