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Search results; Over 1,000 homes in Stockbridge

Hotel in Stockbridge
Walkable Stockbridge + Headed Pool & Bike Rentals
2 bedrooms, 4 beds, 1 private bathroom
20–25 Sept
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Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 bathrooms
13–18 Sept
4.89 out of 5 average rating, 254 reviews
Guest favourite
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.89 out of 5 average rating, 127 reviews
Guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds, 2.5 bathrooms
27 Oct – 1 Nov
4.95 out of 5 average rating, 189 reviews
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
14–19 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
3 bedrooms, 4 beds, 2 bathrooms
17–22 Oct
4.99 out of 5 average rating, 87 reviews
Top guest favourite
Home in Lee
Stylish Mid-century Modern Berkshires Cape
4 bedrooms, 5 beds, 2.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 143 reviews
Superhost
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Stockbridge
Allen House Berkshires 7BR House with Pool
7 bedrooms, 9 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 168 reviews
Guest favourite
Home in Stockbridge
Beachwood Cottage
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Stockbridge
Historic Stockbridge Villa on 25 acres
11 bedrooms, 16 beds, 6.5 bathrooms
27 Oct – 1 Nov
4.96 out of 5 average rating, 67 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Stockbridge
Autumn in Stockbridge
3 bedrooms, 6 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Stockbridge
Meadow's Edge - Modern Retreat w/ In Law Suite
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Stockbridge
Tranquil 3 BR Stockbridge House w/ Private Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Oct
4.87 out of 5 average rating, 63 reviews