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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
20–25 Sept
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4.91 out of 5 average rating, 175 reviews
Top guest favourite
Flat in Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
1 bedroom, 1 queen bed
13–18 Sept
4.96 out of 5 average rating, 124 reviews
Guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds
27 Oct – 1 Nov
4.95 out of 5 average rating, 189 reviews
Guest favourite
Cabin in Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
3 bedrooms, 5 beds
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
13–18 Sept
4.89 out of 5 average rating, 127 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, 61 reviews
Top guest favourite
Home in Stockbridge
Stockbridge pied-à-terre
1 bedroom, 1 king bed
10–15 Nov
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds
22–27 Sept
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
2 bedrooms, 2 queen beds
14–19 Sept
4.94 out of 5 average rating, 168 reviews
Top guest favourite
Home in Stockbridge
Secluded Family Home in Serene Stockbridge Woods
3 bedrooms, 4 beds
17–22 Oct
4.99 out of 5 average rating, 87 reviews
Guest favourite
Home in Stockbridge
Your Stockbridge Getaway
5 bedrooms, 8 beds
14–19 Sept
4.96 out of 5 average rating, 28 reviews
Barn in West Stockbridge
Berkshires Barn Stay on Working Homestead
2 bedrooms, 3 beds
15–20 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Stockbridge
Beachwood Cottage
3 bedrooms, 3 beds
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Lee
Spacious Central Berkshires Home for Groups
4 bedrooms, 5 beds
13–18 Sept
4.89 out of 5 average rating, 54 reviews
Guest favourite
Home in Stockbridge
Tranquil 3 BR Stockbridge House w/ Private Deck!
3 bedrooms, 4 beds
26–31 Oct
4.87 out of 5 average rating, 63 reviews
Guest favourite
Home in Stockbridge
Allen House Berkshires 7BR House with Pool
7 bedrooms, 9 beds
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Stockbridge
New England Family Retreat in Stockbridge, MA
4 bedrooms, 5 beds
28 Sept – 3 Oct
4.83 out of 5 average rating, 89 reviews
Guest favourite
Home in Stockbridge
Cozy, welcoming Berkshires cabin – come unplug!
2 bedrooms, 4 beds
4–9 Oct
4.85 out of 5 average rating, 27 reviews