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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
12–17 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
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
24–29 Sept
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Richmond
Classic New England Home with direct trail access
4 bedrooms, 5 beds
12–17 Sept
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 37 reviews
Home in Richmond
Josiah Loomis 1832 Homestead
3 bedrooms, 3 beds
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
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
21–26 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Pittsfield
Berkshires Colonial on 2 Acres by Evergreen Home
4 bedrooms, 9 beds
4–9 Oct
5.0 out of 5 average rating, 57 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds
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
25–30 Oct
4.96 out of 5 average rating, 77 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds
12–17 Sept
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds
12–17 Oct
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 108 reviews
Superhost
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds
12–17 Sept
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Pittsfield
Entire Historic Farmhouse, 5 BR
5 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Pittsfield
Modern, Renovated Lakefront Escape
4 bedrooms, 6 beds
15–20 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds
22–27 Sept
4.98 out of 5 average rating, 64 reviews
Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds
23–28 Sept
4.91 out of 5 average rating, 187 reviews