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Search results; Over 1,000 homes in Stockbridge

Guest favourite
Home in Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
2 bedrooms, 2 beds, 1 private bathroom
23–28 Aug
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4.94 out of 5 average rating, 161 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed
23–28 Aug
4.85 out of 5 average rating, 157 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds
7–12 Sept
4.96 out of 5 average rating, 308 reviews
Guest favourite
Flat in Stockbridge
Stockbridge private apartment
1 bedroom, 2 beds
6–11 Sept
4.93 out of 5 average rating, 95 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 31 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
23–28 Aug
4.48 out of 5 average rating, 27 reviews
Guest favourite
Room in Pittsfield
Romantic King Room in Downtown Victorian
1 bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 56 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Lee
GreenHouse
2 bedrooms, 2 beds
24–29 Oct
4.99 out of 5 average rating, 134 reviews
Guest favourite
Flat in Lee
Cozy Berkshire Cottage Style Apartment
1 bedroom, 2 single beds
23–28 Aug
4.78 out of 5 average rating, 129 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
30 Aug – 4 Sept
4.85 out of 5 average rating, 27 reviews
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
26–31 Oct
4.95 out of 5 average rating, 421 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, 50 reviews
Flat in Stockbridge
Historic Retreat
1 bedroom, 1 queen bed
9–14 Aug
4.86 out of 5 average rating, 59 reviews
Guest favourite
Home in Lee
Stylish Berkshires Retreat
2 bedrooms, 2 queen beds
22–27 Aug
5.0 out of 5 average rating, 10 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
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed
23–28 Aug
4.88 out of 5 average rating, 130 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, 187 reviews