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Search results; Over 1,000 homes in East Chatham

Guest favourite
Barn in East Chatham
Luxury Barn Retreat Near Hudson & the Berkshires
3 bedrooms, 6 beds, 3 private bathrooms
18–23 Aug
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4.96 out of 5 average rating, 111 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
Top guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed
23–28 Aug
4.87 out of 5 average rating, 175 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, 180 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds
23–28 Aug
4.96 out of 5 average rating, 192 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, 284 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, 31 reviews
Top guest favourite
Home in New Lebanon
The old sawmill from 1771
1 bedroom, 2 beds
5–10 Sept
4.99 out of 5 average rating, 384 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 Niverville
Cozy Lakeside Retreat
2 bedrooms, 2 queen beds
28 Aug – 2 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds
21–26 Sept
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
2 bedrooms, 2 queen beds
23–28 Aug
4.97 out of 5 average rating, 201 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds
24–29 Aug
4.94 out of 5 average rating, 214 reviews
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
3 bedrooms, 6 beds
31 Aug – 5 Sept
4.94 out of 5 average rating, 52 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, 371 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 313 reviews
Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
3 bedrooms, 4 beds
8–13 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Guest house in Stuyvesant
The Falls at Lindenwald Cottage
1 bedroom, 2 beds
7–12 Sept
5.0 out of 5 average rating, 72 reviews