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Search results; Over 1,000 homes in Richmond

Top 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, 205 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Richmond
Classic New England Home with a Swimming Pool
4 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 16 reviews
Home in Richmond
Berkshires Chalet Mins to Tanglewood/Lenox
4 bedrooms, 7 beds, 3 bathrooms
11–16 Aug
4.75 out of 5 average rating, 4 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Richmond
Richmond Pond All Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Richmond
Minutes to Tanglewood with Massive Backyard
5 bedrooms, 7 beds, 2.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 39 reviews
Guest favourite
Cottage in Pittsfield
Charming lakeview cottage w/ kayaks, Richmond Pond
3 bedrooms, 4 beds, 1 bathroom
3–8 Sept
4.81 out of 5 average rating, 54 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, 35 reviews
Top guest favourite
Guest suite in Richmond
Berkshire Mountain Retreat
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 49 reviews
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, 20 reviews
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Aug
5.0 out of 5 average rating, 22 reviews
Home in Stockbridge
Stockbridge Home: Walk to Town Beach!
3 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
4.85 out of 5 average rating, 34 reviews
Guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.9 out of 5 average rating, 41 reviews
Home in Lenox
The Gardener's Cottage 1893 at Ventfort Hall
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 32 reviews
Guest favourite
Chalet in Lenox
Modern Chalet Near Tanglewood & Downtown Lenox
3 bedrooms, 4 beds, 3 bathrooms
6–11 Sept
4.89 out of 5 average rating, 44 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 171 reviews
Top guest favourite
Cabin in Stockbridge
Lakeshore cabin with beach and dock
3 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.98 out of 5 average rating, 64 reviews