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Search results; Over 1,000 homes in Richmond

Guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.94 out of 5 average rating, 201 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
3–9 Aug
4.96 out of 5 average rating, 28 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
13–18 Jul
Top guest favourite
Home in Richmond
"Hemlock Shadow" near Tanglewood on Six Acres
4 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 19 reviews
Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
4.5 out of 5 average rating, 6 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
5–10 Aug
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 25 reviews
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 199 reviews
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds, 2.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Pittsfield
Modern, Renovated Lakefront Escape
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
3–8 Sept
4.8 out of 5 average rating, 51 reviews
Guest favourite
Home in Pittsfield
Ski the Berkshires at Hygge House on Richmond Pond
3 bedrooms, 4 beds, 2 bathrooms
26 Jul – 2 Aug
4.96 out of 5 average rating, 72 reviews
Guest favourite
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Richmond
Gated Mansion, Heated Pool, Mini Gym- Sleeps 11!
5 bedrooms, 9 beds, 5 bathrooms
14–19 Mar
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.91 out of 5 average rating, 182 reviews