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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, 122 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 47 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.84 out of 5 average rating, 153 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
4.96 out of 5 average rating, 302 reviews, 2 beds, 1 bathroom
7–12 Sept
Home in Stockbridge
Light-filled Carpenter's Cottage
New place to stay, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Room in Lenox
Heart of the Shire! ~ Private room w/shared bath
4.97 out of 5 average rating, 63 reviews, 1 double bed, 1 bathroom
21–26 Jul
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Home in Lee
Berkshire 4 season home
4.98 out of 5 average rating, 248 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.92 out of 5 average rating, 92 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Room in Lenox
Room with shared bath LenoxDale MA.
5.0 out of 5 average rating, 18 reviews, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
4.95 out of 5 average rating, 183 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Sept
Flat in Stockbridge
Historic Retreat
4.86 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Guest suite in Stockbridge
Private Stockbridge Getaway
4.97 out of 5 average rating, 69 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Jul – 4 Aug
Home in Stockbridge
Light Filled - Modern Rustic Home
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
4.91 out of 5 average rating, 150 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest house in West Stockbridge
Guest House 15 mins to Tanglewood
5.0 out of 5 average rating, 31 reviews, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
4.91 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
4.95 out of 5 average rating, 151 reviews, 3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug