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Search results; Over 1,000 homes in Richmond

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Guest favourite
Home in Richmond
Classic New England Home with direct trail access
4 bedrooms, 5 beds, 2.5 private bathrooms
16–21 Sept
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4.95 out of 5 average rating, 20 reviews
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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
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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
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Guest favourite
Guest suite in Richmond
Berkshires/Pet Friendly/Tanglewood/Private Ranch
2 bedrooms, 3 queen beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 207 reviews
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Top guest favourite
Home in Pittsfield
Friendly Hills | Passive Home • EV Charger
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
4.91 out of 5 average rating, 47 reviews
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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
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Guest favourite
Home in West Stockbridge
Rustic Modern Retreat
3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Sept
4.92 out of 5 average rating, 73 reviews
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Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
3 bedrooms, 3 beds, 2.5 bathrooms
30 Oct – 4 Nov
4.95 out of 5 average rating, 111 reviews
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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
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Home in Canaan
Cozy 3-bedroom chalet with mountain views
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
New place to stay
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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
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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
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Guest favourite
Cottage in Pittsfield
Pine & Paddle | Pond Access • Kayaks
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Oct
4.91 out of 5 average rating, 22 reviews
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Superhost
Home in Lenox
Belden Farm - WALK to Tanglewood !
6 bedrooms, 7 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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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, 207 reviews
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Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
19–24 Oct
4.97 out of 5 average rating, 63 reviews
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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
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Top guest favourite
Home in Lenox
Lenox cottage 1 mile from town center 2 bed 2 bath
2 bedrooms, 2 beds, 1 bathroom
13–18 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 10 reviews