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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.91 out of 5 average rating, 160 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
4.84 out of 5 average rating, 154 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Home in Stockbridge
Light-filled Carpenter's Cottage
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
4.92 out of 5 average rating, 93 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
4.98 out of 5 average rating, 48 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Sept
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
Guest favourite
Room in Lenox
Cozy Private room w/Private bath, Lenoxdale, MA
4.97 out of 5 average rating, 31 reviews, 1 double bed, 1 bathroom
2–7 Aug
Room in Stockbridge
Iris Room bright with 4 windows :)
4.36 out of 5 average rating, 45 reviews, 1 bed, 1 bathroom
1–6 Aug
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
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
Top guest favourite
Cottage in Great Barrington
Artist Cottage
4.93 out of 5 average rating, 346 reviews, 1 bedroom, 1 bed, 2 bathrooms
2–7 Aug
Guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
4.89 out of 5 average rating, 45 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
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
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
Guest suite in Stockbridge
Private Stockbridge Getaway
4.97 out of 5 average rating, 69 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Guest favourite
Flat in Great Barrington
King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi
4.88 out of 5 average rating, 163 reviews, 1 bed, 1 bathroom
1–6 Aug
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
4.85 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
4.94 out of 5 average rating, 212 reviews, 1 bedroom, 1 bed, 1 bathroom
22–27 Aug
Guest favourite
Flat in Great Barrington
Beautfiul, modern, GB apartment
4.81 out of 5 average rating, 300 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Oct