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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Tiny home in Chatham
Peaceful Tiny House Escape by Hudson & Berkshires
2 bedrooms, 2 beds, 1 shared bathroom
18–23 Sept
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4.99 out of 5 average rating, 286 reviews
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Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 379 reviews
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Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
1 bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 105 reviews
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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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Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 9 reviews
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Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
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Flat in Chatham
Chatham Village Library Flat
2 bedrooms, 3 beds, 1 bathroom
1–6 Dec
4.88 out of 5 average rating, 8 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
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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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Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 84 reviews
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Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Oct
4.89 out of 5 average rating, 35 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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Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 196 reviews
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Home in Ghent
Blacksmith House - Charming Historic Getaway
3 bedrooms, 2 queen beds, 2 bathrooms
1–6 Feb
4.95 out of 5 average rating, 154 reviews
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Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 83 reviews
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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 Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 288 reviews
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Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 12 reviews
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Townhouse in Hudson
Chic Hot Tub Escape | PetFriendly | Hudson, NY
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 115 reviews