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Search results; Over 1,000 homes in East Chatham

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Top guest favourite
Cabin in East Chatham
The Cabin at Whispering Pines - on 34 acres
2 bedrooms, 2 beds, 1 private bathroom
26–31 Oct
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4.98 out of 5 average rating, 62 reviews
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Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds, 2 bathrooms
14–19 Oct
5.0 out of 5 average rating, 35 reviews
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Guest favourite
Home in Old Chatham
Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 56 reviews
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Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in East Chatham
Secluded Chatham Oasis-Hot Tub+Treehouse+Pets
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
19–24 Oct
4.97 out of 5 average rating, 63 reviews
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Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 191 reviews
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Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Home in New Lebanon
Modernized 1860s Getaway w/ Queechy Lake Passes*
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 27 reviews
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Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 179 reviews
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Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 53 reviews
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Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds, 3.5 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 18 reviews
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Home in Canaan
Peaceful Berkshire Getaway (A/C, Lake Access)
4 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Chatham
A unique village home steps to shops, café, nature
4 bedrooms, 4 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Chatham
spencertown farm house
5 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 88 reviews
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Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 83 reviews
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Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Nov
4.95 out of 5 average rating, 289 reviews