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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
Guest favourite
Cottage in Old Chatham
Charming upstate cottage close to Berkshires
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Jun
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 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
3–8 Aug
Guest favourite
Home in Old Chatham
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
4.95 out of 5 average rating, 282 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 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
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
Cabin in East Nassau
Summer Mountain Retreat + Views, Fire Pit, Hot Tub
4.98 out of 5 average rating, 99 reviews, 3 bedrooms, 3 beds, 2 bathrooms
17–22 Sept
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Malden Bridge
Lovely 1790 Hudson Valley Farmhouse with Pool
4.9 out of 5 average rating, 91 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 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
6–11 Sept
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
18–23 Aug
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
4.97 out of 5 average rating, 60 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
Guest favourite
Chalet in Canaan
Sunset Ridge Chalet•Berkshires• Queechy Lake•HRV
4.89 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 3 bathrooms
2–7 Aug
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
Guest house in Chatham
Tranquil Guest House, Chatham NY
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
Tiny home in Chatham
Sugar Shack | Romantic Tiny Home + Hot Tub
4.99 out of 5 average rating, 505 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug