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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
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, 157 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 308 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.93 out of 5 average rating, 95 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 12 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.48 out of 5 average rating, 27 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, 134 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
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.95 out of 5 average rating, 421 reviews
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 212 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Place to stay in Lenox
Private outbuilding retreat room at Eastover
1 bedroom, 2 beds, 1 bathroom
13–18 Aug
4.5 out of 5 average rating, 12 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
30 Aug – 4 Sept
4.91 out of 5 average rating, 55 reviews
Room in Lenox
Standard Queen at Hideaway Inn Lenox
1 queen bed, 1 bathroom
22–27 Aug
New place to stay
Guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 200 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
Guest favourite
Flat in Lee
Cozy Berkshire Cottage Style Apartment
1 bedroom, 2 single beds, 1 bathroom
23–28 Aug
4.78 out of 5 average rating, 129 reviews