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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 private bathrooms
30 Aug – 4 Sept
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4.89 out of 5 average rating, 248 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 134 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
Flat in Stockbridge
Quaint & cozy loft
1 bedroom, 1 queen bed
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
6–11 Sept
4.93 out of 5 average rating, 95 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds
7–12 Sept
4.96 out of 5 average rating, 309 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
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed
23–28 Aug
4.85 out of 5 average rating, 158 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
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
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds
13–18 Sept
4.95 out of 5 average rating, 185 reviews
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
3 bedrooms, 4 beds
14–19 Aug
4.85 out of 5 average rating, 34 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
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed
24–31 Aug
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
9–14 Aug
4.96 out of 5 average rating, 225 reviews
Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.9 out of 5 average rating, 166 reviews
Guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds
22–27 Aug
5.0 out of 5 average rating, 10 reviews