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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
23–28 Aug
4.85 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
23–28 Aug
4.91 out of 5 average rating, 175 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
25–30 Sept
4.99 out of 5 average rating, 326 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
4–9 Oct
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
30 Oct – 4 Nov
4.93 out of 5 average rating, 350 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 135 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
23–28 Aug
4.48 out of 5 average rating, 29 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
14–19 Sept
4.93 out of 5 average rating, 95 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed
5–10 Sept
4.96 out of 5 average rating, 124 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Lee
Eliza Suite
1 bedroom, 1 bed
14–19 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds
23–28 Aug
4.94 out of 5 average rating, 47 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 58 reviews
Camper van/Motorhome in Sandisfield
Camper tucked into the woods
1 bedroom, 2 beds
16–21 Aug
New place to stay
Top guest favourite
Guest house in Lenox
The East Street Cabin
1 queen bed
23–28 Aug
4.94 out of 5 average rating, 124 reviews