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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, 4 beds, 3 private bathrooms
10–15 Aug
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4.97 out of 5 average rating, 109 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
4.97 out of 5 average rating, 601 reviews, 1 king bed, 1 bathroom
19–24 Jul
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
26–31 Jul
Top guest favourite
Guest house in Chatham
Tranquil Guest House, Chatham NY
4.94 out of 5 average rating, 52 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
4.98 out of 5 average rating, 281 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
4.86 out of 5 average rating, 170 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
4.94 out of 5 average rating, 395 reviews, 1 queen bed, 1 bathroom
12–17 Jul
Guest favourite
Room in Old Chatham
Haddock Hill House
4.89 out of 5 average rating, 53 reviews, 2 beds, 1 bathroom
10–15 Jul
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 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
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Old Chatham
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Rooms in Pittsfield
Equestrian retreat
4.96 out of 5 average rating, 199 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
4.99 out of 5 average rating, 314 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Home in Old Chatham
The Red House
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Sept
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
4.99 out of 5 average rating, 310 reviews, 3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
5.0 out of 5 average rating, 97 reviews, 1 bed, 1 bathroom
31 Jul – 5 Aug