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Search results; Over 1,000 homes in East Chatham

Top guest favourite
Barn in East Chatham
Luxury Barn Retreat on Private Wooded Acres
3 bedrooms, 6 beds, 3 private bathrooms
10–15 Aug
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4.97 out of 5 average rating, 109 reviews
Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
4.87 out of 5 average rating, 171 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Flat in East Chatham
Bennett Abode
4.96 out of 5 average rating, 175 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
2–7 Aug
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
4.95 out of 5 average rating, 284 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
4.97 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
4.97 out of 5 average rating, 607 reviews, 1 king bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 311 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
5.0 out of 5 average rating, 31 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Sept
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
4.98 out of 5 average rating, 285 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
4.94 out of 5 average rating, 214 reviews, 2 bedrooms, 2 beds, 1 bathroom
4–9 Aug
Top guest favourite
Barn in Stuyvesant
Pond Side R & R
5.0 out of 5 average rating, 135 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Aug
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.97 out of 5 average rating, 200 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
4.94 out of 5 average rating, 400 reviews, 1 queen bed, 1 bathroom
10–15 Aug
Top guest favourite
Home in Niverville
Cozy Lakeside Retreat
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
Top guest favourite
Home in Ghent
Blacksmith House - Charming Historic Getaway
4.95 out of 5 average rating, 151 reviews, 3 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
4.97 out of 5 average rating, 61 reviews, 3 bedrooms, 3 beds, 3 bathrooms
8–13 Sept