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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, 310 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, 58 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, 163 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 618 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, 327 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, 33 reviews
Guest favourite
Flat in Great Barrington
King Bed|2m Ski Resort|Stylish|Fast Wi-Fi
1 king bed
23–28 Aug
4.89 out of 5 average rating, 91 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
14–19 Sept
4.92 out of 5 average rating, 97 reviews
Guest favourite
Flat in Lee
Cozy Berkshire Cottage Style Apartment
1 bedroom, 2 single beds
25–30 Aug
4.77 out of 5 average rating, 131 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 135 reviews
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed
22–27 Aug
4.84 out of 5 average rating, 61 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
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, 34 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
6–11 Sept
4.91 out of 5 average rating, 58 reviews
Guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
23–28 Aug
4.87 out of 5 average rating, 261 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed
23–28 Aug
4.88 out of 5 average rating, 133 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
Guest favourite
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.91 out of 5 average rating, 169 reviews