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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 bed, 1 private bathroom
5–10 Sept
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4.96 out of 5 average rating, 124 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, 160 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 309 reviews
Room in Stockbridge
Iris Room bright with 4 windows :)
1 bed, 1 bathroom
23–28 Aug
4.33 out of 5 average rating, 48 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
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 212 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
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
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed, 1 bathroom
10–15 Aug
4.94 out of 5 average rating, 402 reviews
Top guest favourite
Room in Pittsfield
2-Rm Suite in the Berkshires - private BR and Den
1 queen bed, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 88 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
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 349 reviews
Top guest favourite
Room in Becket
East b.r. in upstairs suite of open plan home
1 bathroom
30 Aug – 4 Sept
4.87 out of 5 average rating, 259 reviews
Guest favourite
Room in Lenox
Cozy Private room w/Private bath, Lenoxdale, MA
1 double bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Flat in Stockbridge
Two bedrooms in Charming Berkshires Farmhouse
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 154 reviews
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.85 out of 5 average rating, 60 reviews