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Search results; Over 1,000 homes in Chatham

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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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Home in Ghent
The Wool House - Luxe Hudson Farmhouse on 3 acres
4 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 23 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 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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Guest house in Stuyvesant
The Falls at Lindenwald Cottage
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 75 reviews
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Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
16–21 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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Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
17–22 Sept
4.96 out of 5 average rating, 196 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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Home in Austerlitz
Private cottage close to shopping, dining, skiing.
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
8–15 Nov
4.98 out of 5 average rating, 83 reviews
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Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 24 reviews
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Cottage in Niverville
Huge Lakefront, Cozy Private Cottage in Upstate NY
2 bedrooms, 2 queen beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 52 reviews
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Home in Hudson
Rushing Rapids Cottage – a birdwatcher's paradise
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 415 reviews
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Cottage in Ghent
Light, airy cottage with pool 10 min from Hudson
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.79 out of 5 average rating, 19 reviews
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Home in Ghent
Hawthorne Valley Barn
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
4.97 out of 5 average rating, 36 reviews