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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Tiny home in Chatham
Sugar Shack | Romantic Tiny Home + Hot Tub
1 bedroom, 1 bed, 1 private bathroom
7–12 Nov
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4.99 out of 5 average rating, 515 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, 381 reviews
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Serviced apartment 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, 65 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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Guest favourite
Serviced apartment in Chatham
Boutique Apt 1-BR in Historic Chatham Landmark
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.83 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
1–6 Oct
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
1–6 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Chatham
Writer's Retreat in the Woods
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
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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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 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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Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
8–13 Dec
5.0 out of 5 average rating, 36 reviews
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Home in Chatham
spencertown farm house
5 bedrooms, 8 beds, 2.5 bathrooms
1–6 Oct
4.97 out of 5 average rating, 88 reviews
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Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 85 reviews
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Top guest favourite
Cabin in Chatham
Rustic Secluded Cabin near Berkshires. *wood stove
4 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
4.92 out of 5 average rating, 146 reviews
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Top guest favourite
Home in Ghent
Luxe Retreat+Sauna+HotTub & Swimming on 12 acres
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 135 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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Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 196 reviews