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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
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
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 618 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, 57 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, 327 reviews
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.84 out of 5 average rating, 61 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
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
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
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
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, 131 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
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
30 Oct – 4 Nov
4.93 out of 5 average rating, 351 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 133 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 154 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed, 2 bathrooms
6–11 Sept
4.91 out of 5 average rating, 58 reviews
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, 6 reviews
Top guest favourite
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed, 1 bathroom
24–31 Aug
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 47 reviews