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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, 251 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
23–28 Aug
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
23–28 Aug
4.85 out of 5 average rating, 163 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 124 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, 135 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
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 622 reviews
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
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
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 58 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
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed, 1 bathroom
23–28 Aug
4.83 out of 5 average rating, 112 reviews
Guest favourite
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
3 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.89 out of 5 average rating, 125 reviews
Superhost
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 98 reviews
Top guest favourite
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed, 1 bathroom
24–31 Aug
4.95 out of 5 average rating, 42 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Stockbridge
Stockbridge: Summer/Fall 3BR/2BA Cottage with Lake
3 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.86 out of 5 average rating, 21 reviews