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Search results; Over 1,000 homes in Old Chatham

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Top guest favourite
Home in Old Chatham
The Red House
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Nov
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4.99 out of 5 average rating, 85 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 Old Chatham
Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 56 reviews
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Home in Old Chatham
1790s Farmhouse on 70 Acres with Saltwater Pool
6 bedrooms, 6 beds, 3.5 bathrooms
26 Sept – 1 Oct
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Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds, 2.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 24 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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Superhost
Guest house in Old Chatham
Acorn Cottage-guest cottage private views & trails
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Jan
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Guest favourite
Home in Old Chatham
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Cottage in Old Chatham
Cozy Cottage Retreat
1 bedroom, 4 beds, 1 bathroom
23–28 Oct
4.93 out of 5 average rating, 14 reviews
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Top guest favourite
Guest house in Old Chatham
Mountain View Retreat in Hudson Valley
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 32 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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Superhost
Rooms in Niverville
Private 2 Queen Rooms, Bath w/Breakfast & Fire Pit
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Oct
New place to stay
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Top guest favourite
Cottage in Averill Park
Cozy cottage with pool, walking distance to lake
3 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 171 reviews
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Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
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Top guest favourite
Cabin in Spencertown
Wake Up in the Woods · A Cozy Fall Escape
3 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
3 bedrooms, 6 beds, 1 bathroom
23–28 Sept
4.94 out of 5 average rating, 54 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
Home in Malden Bridge
Luxe upstate retreat with sauna on 20 acres
4 bedrooms, 6 beds, 3.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 28 reviews