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Search results; Over 1,000 homes in Stockbridge

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Guest favourite
Home in Stockbridge
Rabbit Run in the heart of Stockbridge Village
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.89 out of 5 average rating, 127 reviews
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Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed, 1 bathroom
29 Sept – 4 Oct
4.96 out of 5 average rating, 124 reviews
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Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 61 reviews
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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, 190 reviews
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Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds, 2.5 bathrooms
16–21 Sept
4.96 out of 5 average rating, 28 reviews
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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
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Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 254 reviews
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Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Sept
4.94 out of 5 average rating, 168 reviews
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Top guest favourite
Home in Stockbridge
Relaxing Berkshire Retreat with Lake Access
3 bedrooms, 4 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed, 1 bathroom
16–21 Nov
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Guest house in Stockbridge
Modern barn in the heart of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 175 reviews
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Guest favourite
Home in Stockbridge
Light-filled Carpenter's Cottage
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 6 reviews
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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
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Guest favourite
Home in Stockbridge
Stockbridge Cape Near Tanglewood!
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.94 out of 5 average rating, 48 reviews
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Top guest favourite
Guest house in West Stockbridge
Guest House near hiking trails and excellent cafés
2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Stockbridge
Tranquil 3 BR Stockbridge House w/ Private Deck!
3 bedrooms, 4 beds, 1.5 bathrooms
31 Oct – 5 Nov
4.87 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 37 reviews
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Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.9 out of 5 average rating, 10 reviews