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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
15–20 Aug
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4.96 out of 5 average rating, 111 reviews
Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed
9–14 Aug
4.87 out of 5 average rating, 173 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, 12 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds
23–28 Aug
4.97 out of 5 average rating, 190 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed
23–28 Aug
4.96 out of 5 average rating, 178 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, 54 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
Guest favourite
Cabin in East Nassau
Summer Mountain Retreat + Views, Fire Pit, Hot Tub
3 bedrooms, 3 beds
30 Sept – 5 Oct
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds
13–18 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 bedroom, 1 queen bed
23–28 Aug
4.98 out of 5 average rating, 287 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, 32 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
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 614 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
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
1 bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 103 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, 29 reviews
Top guest favourite
Tiny home in Chatham
Peaceful Tiny House Escape by Hudson & Berkshires
2 bedrooms, 2 queen beds
10–15 Aug
4.99 out of 5 average rating, 282 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, 312 reviews
Guest favourite
Rooms in Canaan
EnSuite: 2 Bedrms/Private Bathrm/breakfast
2 bedrooms, 3 beds
14–19 Aug
4.98 out of 5 average rating, 41 reviews