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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, 160 reviews
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
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 49 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, 93 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
Top guest favourite
Flat in Stockbridge
Three bedroom duplex in Stockbridge on the river
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 53 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, 133 reviews
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.85 out of 5 average rating, 34 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
3 bedrooms, 4 beds, 2 bathrooms
24–31 Aug
4.99 out of 5 average rating, 79 reviews
Home in Stockbridge
Light-filled Carpenter's Cottage
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
New place to stay
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
4.83 out of 5 average rating, 41 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
Home in Stockbridge
Bramaluna
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 3 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
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 154 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 9 reviews