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Search results; Over 1,000 homes in East Chatham

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Guest favourite
Barn in East Chatham
Luxury Barn Retreat Near Hudson & the Berkshires
2 bedrooms, 6 beds, 2 private bathrooms
13–18 Oct
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4.96 out of 5 average rating, 114 reviews
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Top guest favourite
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
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
4.86 out of 5 average rating, 178 reviews
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Top guest favourite
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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Guest favourite
Home in Old Chatham
Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
4 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.95 out of 5 average rating, 56 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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Home in Old Chatham
1790s Farmhouse on 70 Acres with Saltwater Pool
6 bedrooms, 6 beds, 3.5 bathrooms
24–29 Sept
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Top guest favourite
Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in East Chatham
Stylish Rural Sanctuary! (+ Summer Pool)
4 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Room in Old Chatham
Haddock Hill House
2 beds, 1 bathroom
21–26 Sept
4.89 out of 5 average rating, 54 reviews
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Top guest favourite
Home in Old Chatham
The Red House
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
4.99 out of 5 average rating, 85 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 Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 10 reviews
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Guest favourite
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
Flat in Chatham
Private Penthouse Apt in Historic Landmark 3-BR
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
4.97 out of 5 average rating, 64 reviews
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Top guest favourite
Home in East Chatham
Glorious Light and Views!
4 bedrooms, 4 beds, 4 bathrooms
1–6 Jan
5.0 out of 5 average rating, 19 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
Home in East Chatham
Secluded Chatham Oasis-Hot Tub+Treehouse+Pets
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 43 reviews
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Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 36 reviews