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Search results; Over 1,000 homes in Richmond

Top guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 beds, 1 private bathroom
8–13 Sept
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4.94 out of 5 average rating, 207 reviews
Guest favourite
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
19–24 Sept
4.83 out of 5 average rating, 6 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 37 reviews
Home in Richmond
Josiah Loomis 1832 Homestead
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.57 out of 5 average rating, 83 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
10–15 Sept
4.82 out of 5 average rating, 57 reviews
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
8–13 Sept
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 206 reviews
Guest favourite
Home in Pittsfield
Summer on the Lake - Berkshires near Tanglewood
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 76 reviews
Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.91 out of 5 average rating, 187 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Richmond
Sunshine Cottage
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jan
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds, 1 bathroom
12–17 Oct
4.96 out of 5 average rating, 52 reviews
Guest favourite
Chalet in Lenox
Modern Chalet Near Tanglewood & Downtown Lenox
3 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
4.87 out of 5 average rating, 46 reviews
Superhost
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
4.96 out of 5 average rating, 52 reviews