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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 private bathrooms
30 Aug – 4 Sept
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4.89 out of 5 average rating, 249 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
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
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
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, 55 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, 615 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 40 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
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 185 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
Top guest favourite
Flat in Lee
Eliza Suite
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 31 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds, 1.5 bathrooms
20–25 Aug
5.0 out of 5 average rating, 4 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
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, 124 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 227 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.99 out of 5 average rating, 93 reviews
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 11 reviews