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Search results; Over 1,000 homes in Richmond

Guest favourite
Home in Richmond
Classic New England Home with direct trail access
4 bedrooms, 5 beds, 2.5 private bathrooms
11–16 Sept
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4.95 out of 5 average rating, 20 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
24–29 Sept
4.97 out of 5 average rating, 33 reviews
Guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 queen beds, 1 bathroom
11–16 Sept
4.94 out of 5 average rating, 207 reviews
Home in Richmond
1 Mi to Vineyard: Serene Berkshires Country Escape
4 bedrooms, 4 beds, 2.5 bathrooms
30 Sept – 5 Oct
4.38 out of 5 average rating, 8 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
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 57 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
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
22–27 Sept
4.82 out of 5 average rating, 57 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 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
11–16 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, 77 reviews
Superhost
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
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 26 reviews
Superhost
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
11–16 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Richmond
Richmond Ranch w/ Hot Tub by Evergreen Home
3 bedrooms, 4 beds, 2 bathrooms
2–7 Jan
4.88 out of 5 average rating, 24 reviews
Top guest favourite
Home in Pittsfield
Modern, Renovated Lakefront Escape
4 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
4.95 out of 5 average rating, 42 reviews
Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.91 out of 5 average rating, 187 reviews