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Search results; Over 1,000 homes in Stockbridge

Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 bed, 1 private bathroom
5–10 Sept
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4.96 out of 5 average rating, 124 reviews
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
Modern studio with views of the treetops
2 beds
23–28 Aug
4.96 out of 5 average rating, 310 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 135 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds
13–18 Sept
4.88 out of 5 average rating, 51 reviews
Guest favourite
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, 6 reviews
Top guest favourite
Home in Lenox
Home away from home: Minutes to Tanglewood.
3 bedrooms, 4 beds
28 Sept – 3 Oct
4.93 out of 5 average rating, 55 reviews
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
3 bedrooms, 4 beds
16–21 Oct
4.85 out of 5 average rating, 34 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
14–19 Sept
4.93 out of 5 average rating, 96 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, 618 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, 57 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
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
3 bedrooms, 4 beds
24–29 Aug
4.89 out of 5 average rating, 125 reviews
Top guest favourite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
3 bedrooms, 4 beds
23–28 Aug
4.99 out of 5 average rating, 82 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 40 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
22–27 Aug
4.67 out of 5 average rating, 3 reviews
Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.9 out of 5 average rating, 168 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds
16–21 Aug
New place to stay
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews