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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, 158 reviews
Top guest favourite
Cottage in Stockbridge
Quiet 2 BR cottage in the heart of the Berkshires
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 43 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 90 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, 310 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 181 reviews
Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
4.93 out of 5 average rating, 45 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
4.91 out of 5 average rating, 44 reviews
Superhost
Home in Stockbridge
Mac Shores | 5 min to Tanglewood ! • Shared Beach
3 bedrooms, 4 beds, 1 bathroom
29 Jul – 3 Aug
4.81 out of 5 average rating, 16 reviews
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
3 bedrooms, 4 beds, 2.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 298 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, 122 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.98 out of 5 average rating, 89 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
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
12–17 Jul
4.88 out of 5 average rating, 60 reviews
Guest favourite
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
4.85 out of 5 average rating, 86 reviews
Top guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.83 out of 5 average rating, 6 reviews