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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
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
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
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.89 out of 5 average rating, 37 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
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 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
Top guest favourite
Room in Pittsfield
Large guest suite w/private bath in the Berkshires
2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 464 reviews
Top guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 59 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
23–28 Aug
4.87 out of 5 average rating, 261 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 14 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, 7 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, 203 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
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 239 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 154 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, 424 reviews