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Search results; Over 1,000 homes in East Chatham

Chalet in East Chatham
East Chatham Spacious 5BR House Pool Sauna AC
5 bedrooms, 9 beds, 3 private bathrooms
14–19 Sept
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5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds
1–6 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed
23–28 Aug
4.86 out of 5 average rating, 176 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
3–8 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed
6–11 Sept
4.96 out of 5 average rating, 182 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Austerlitz
Private cottage close to shopping, dining, skiing.
3 bedrooms, 4 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.99 out of 5 average rating, 373 reviews
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
3 bedrooms, 6 beds
8–13 Sept
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds
4–9 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed
23–28 Aug
4.94 out of 5 average rating, 405 reviews
Top guest favourite
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
3 bedrooms, 6 beds
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Chalet in Averill Park
A Hidden Sparrow
4 bedrooms, 4 beds
8–13 Sept
4.94 out of 5 average rating, 101 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
22–27 Sept
4.94 out of 5 average rating, 191 reviews
Top guest favourite
Cabin in East Chatham
The Cabin at Whispering Pines - on 34 acres
2 bedrooms, 2 beds
14–19 Sept
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds
2–7 Nov
4.95 out of 5 average rating, 285 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 622 reviews