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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, 158 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, 309 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
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 28 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, 32 reviews
Top 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
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
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
Flat in Lee
Cozy Berkshire Cottage Style Apartment
1 bedroom, 2 single beds, 1 bathroom
25–30 Aug
4.77 out of 5 average rating, 130 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
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
9–14 Aug
4.87 out of 5 average rating, 259 reviews
Superhost
Home in Lee
Pond House at Middle Way Farm • Sunset Views
3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 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, 50 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 256 reviews
Superhost
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 172 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, 54 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 187 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 22 reviews