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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
7–12 Sept
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4.96 out of 5 average rating, 305 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
4.84 out of 5 average rating, 154 reviews
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
1 bedroom, 1 king bed, 1 bathroom
20–25 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Flat in Great Barrington
King Bed|2mi Ski Resort|Fast Wi-Fi|Studio|
1 king bed, 1 bathroom
2–7 Aug
4.85 out of 5 average rating, 105 reviews
Room in Stockbridge
Iris Room bright with 4 windows :)
1 bed, 1 bathroom
2–7 Aug
4.36 out of 5 average rating, 45 reviews
Guest favourite
Room in Lenox
Cozy Private room w/Private bath, Lenoxdale, MA
1 double bed, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
5–10 Sept
4.96 out of 5 average rating, 123 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 94 reviews
Flat in Stockbridge
Two bedrooms in Charming Berkshires Farmhouse
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 3 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, 346 reviews
Home in Stockbridge
Light-filled Carpenter's Cottage
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
Superhost
Guest house in Stockbridge
Guest House in Stockbridge 3 miles to Tanglewood
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.74 out of 5 average rating, 107 reviews
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.86 out of 5 average rating, 59 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
Top guest favourite
Guest suite in Stockbridge
Private Stockbridge Getaway
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 69 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 311 reviews
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 31 reviews