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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
23–28 Aug
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4.96 out of 5 average rating, 309 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, 161 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 326 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
New place to stay
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, 350 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds, 3 bathrooms
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 reviews
Room in Stockbridge
Iris Room bright with 4 windows :)
1 bed, 1 bathroom
23–28 Aug
4.36 out of 5 average rating, 50 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 175 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, 33 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, 237 reviews
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, 5 reviews
Top guest favourite
Flat in Lee
Eliza Suite
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 32 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, 29 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, 13 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
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, 190 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds, 1 bathroom
24–29 Aug
New place to stay
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