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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 beds, 2.5 private bathrooms
18–23 Oct
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4.95 out of 5 average rating, 185 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
22–27 Aug
New place to stay
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds
30 Aug – 4 Sept
4.89 out of 5 average rating, 250 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
4–9 Oct
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds
23–28 Aug
4.96 out of 5 average rating, 309 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
14–19 Sept
4.93 out of 5 average rating, 95 reviews
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 134 reviews
Superhost
Home in Lee
4BDR Elegant Berkshires Escape | Beaver Creek
4 bedrooms, 5 beds
3–8 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Hotel room in Lee
Endless Family Fun: Pools, Arcade Room & Mini Golf
3 bedrooms
23–28 Aug
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
20–25 Sept
4.94 out of 5 average rating, 190 reviews
Flat in Stockbridge
Quaint & cozy loft
1 bedroom, 1 queen bed
12–17 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 615 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed
5–10 Sept
4.96 out of 5 average rating, 124 reviews
Top guest favourite
Flat in Lenox
Historical Housatonic Street Building
2 bedrooms, 1 king bed
21–26 Sept
5.0 out of 5 average rating, 30 reviews
Home in Lenox
7 Minute Walk to Tanglewood from New 2BR Home
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds
28 Aug – 2 Sept
New place to stay