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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
4.92 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Aug
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
13–18 Jul
Home in Richmond
Richmond Pond All Season Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4.96 out of 5 average rating, 28 reviews, 4 bedrooms, 4 beds, 2 bathrooms
3–9 Aug
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 25 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
4.97 out of 5 average rating, 34 reviews, 4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Richmond
"Hemlock Shadow" near Tanglewood on Six Acres
4.95 out of 5 average rating, 19 reviews, 4 bedrooms, 4 beds, 3 bathrooms
29 Aug – 3 Sept
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
4.8 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
3–8 Sept
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4.5 out of 5 average rating, 6 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
4.96 out of 5 average rating, 47 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Sept
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 199 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Aug
Top guest favourite
Home in Richmond
Gated Mansion, Heated Pool, Mini Gym- Sleeps 11!
5.0 out of 5 average rating, 10 reviews, 5 bedrooms, 9 beds, 5 bathrooms
14–19 Mar
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
4.91 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Top guest favourite
Home in Pittsfield
Modern, Renovated Lakefront Escape
4.95 out of 5 average rating, 42 reviews, 4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
Home in New Lebanon
Above the Clouds Mountain Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 4 bathrooms
14–19 Jul
Home in Pittsfield
Cozy Berkshire Lakeside Retreat | Deck + Fire Pit
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Jul