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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
20–25 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
24–29 Sept
4.97 out of 5 average rating, 33 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
Classic New England Home with direct trail access
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.95 out of 5 average rating, 20 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
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 37 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 39 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 Pittsfield
Summer on the Lake - Berkshires near Tanglewood
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 77 reviews
Bed and breakfast in Lenox
Secluded on Main Street: Ludlow Cottage
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
New place to stay
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
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
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, 53 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 53 reviews
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 26 reviews
Superhost
Chalet in Lenox
Modern Chalet Near Tanglewood & Downtown Lenox
3 bedrooms, 4 beds, 3 bathrooms
12–17 Oct
4.87 out of 5 average rating, 46 reviews
Guest favourite
Home in New Lebanon
The Spencer House 7 Bedroom Berkshire Inn
7 bedrooms, 9 beds, 7 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 24 reviews