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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Cottage in Stockbridge
Rustic Berkshires Cottage
2 bedrooms, 2 beds, 1 private bathroom
26 Nov – 1 Dec
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4.9 out of 5 average rating, 20 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
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 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, 46 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
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 170 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
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.86 out of 5 average rating, 58 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
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 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
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
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.83 out of 5 average rating, 88 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
Home in Stockbridge
Bramaluna
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.89 out of 5 average rating, 246 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
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