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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
Studio, 2 beds, 1 shared bathroom
7–12 Sept
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4.96 out of 5 average rating, 310 reviews
Top guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.85 out of 5 average rating, 163 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
5–10 Sept
4.96 out of 5 average rating, 124 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 bathrooms
7–12 Sept
4.89 out of 5 average rating, 251 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 27 reviews
Superhost
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 99 reviews
Guest favourite
Home in Stockbridge
Stockbridge Landings | 3 Mins To Tanglewood
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
30 Oct – 4 Nov
4.93 out of 5 average rating, 351 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
New place to stay
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 188 reviews
Home in Richmond
Ellie’s Overlook, best view in the Berkshires!
3 bedrooms, 3 queen beds, 2 bathrooms
8–13 Sept
New place to stay
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House near hiking trails and excellent cafés
2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
6–11 Sept
4.89 out of 5 average rating, 38 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 248 reviews