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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
23–28 Aug
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4.9 out of 5 average rating, 155 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
Flat in Stockbridge
Quaint & cozy loft
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
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
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
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 45 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, 180 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, 43 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, 84 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
16–21 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 342 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 bathrooms
9–14 Aug
4.89 out of 5 average rating, 245 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, 121 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Stockbridge
Cottage with exquisite views
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 596 reviews
Superhost
Home in Stockbridge
Moss's Muse: A Modern Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Jul
New place to stay
Guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 7 reviews