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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 beds, 2.5 private bathrooms
13–18 Sept
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4.95 out of 5 average rating, 184 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds
25–30 Aug
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
2–7 Aug
4.93 out of 5 average rating, 94 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 133 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds
3–8 Sept
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Stockbridge
Three bedroom duplex in Stockbridge on the river
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds
23–28 Aug
4.94 out of 5 average rating, 47 reviews
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed
2–7 Aug
4.89 out of 5 average rating, 170 reviews
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
3 bedrooms, 4 beds
22–27 Aug
4.85 out of 5 average rating, 34 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds
13–18 Sept
4.88 out of 5 average rating, 50 reviews
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed
24–31 Aug
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 607 reviews
Top guest favourite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
3 bedrooms, 4 beds
24–31 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
6–11 Sept
4.99 out of 5 average rating, 321 reviews
Top guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
1 bedroom, 1 king bed
20–25 Aug
4.92 out of 5 average rating, 24 reviews