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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 bedrooms, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.98 out of 5 average rating, 160 reviews
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Top guest favourite
Cabin in Chatham
A-Frame + Private Hot Tub + Walk to Main St
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
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
Flat 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
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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Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
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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Guest favourite
Home in Chatham
Writer's Retreat in the Woods
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 48 reviews
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Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 36 reviews
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Guest favourite
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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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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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
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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Top guest favourite
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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Top guest favourite
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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Top guest favourite
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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Top guest favourite
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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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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Guest favourite
Rooms in Kinderhook
Kinderhook Farmhouse w/ Pool!!
2 bedrooms, 2 beds, 2 bathrooms
19–24 Sept
4.86 out of 5 average rating, 28 reviews