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Search results; Over 1,000 homes in Old Chatham

Top guest favourite
Home in Old Chatham
The Red House
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Sept
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4.99 out of 5 average rating, 83 reviews
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds
8–13 Sept
5.0 out of 5 average rating, 33 reviews
Home in Old Chatham
1790s Farmhouse on 70 Acres with Saltwater Pool
6 bedrooms, 6 beds
16–21 Sept
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Old Chatham
Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
4 bedrooms, 5 beds
5–10 Sept
4.94 out of 5 average rating, 52 reviews
Guest favourite
Room in Old Chatham
Haddock Hill House
2 beds
30 Aug – 4 Sept
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Old Chatham
Mountain View Retreat in Hudson Valley
2 bedrooms, 3 beds
24–29 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Cottage in Old Chatham
Cozy Cottage Retreat
1 bedroom, 4 beds
1–6 Oct
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed
23–28 Aug
4.94 out of 5 average rating, 405 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 622 reviews
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 bedroom, 1 queen bed
6–11 Sept
4.98 out of 5 average rating, 290 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed
6–11 Sept
4.96 out of 5 average rating, 183 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed
25–30 Sept
4.99 out of 5 average rating, 328 reviews
Top guest favourite
Cabin in East Chatham
The Cabin at Whispering Pines - on 34 acres
2 bedrooms, 2 beds
14–19 Sept
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Nassau
Country Two Bedroom Apartment with full breakfast
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 274 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds
4–9 Nov
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Guest house in Chatham
Tranquil Guest House, Chatham NY
2 bedrooms, 3 beds
1–6 Mar
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds
2–7 Nov
4.95 out of 5 average rating, 286 reviews