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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 shared bathrooms
26–31 Oct
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4.97 out of 5 average rating, 173 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Room in Chatham
Nantucket House of Chatham - Chatham Room
1 king bed, 1 bathroom
16–21 Oct
4.95 out of 5 average rating, 190 reviews
Cabin in Chatham
Pleasant Forest Shores - Cottage #1 - S Chatham
1 bedroom, 2 single beds, 1 bathroom
18–23 Sept
4.7 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Chatham
Chatham Studio- short walk to beach
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Chatham
Forbes, a South Chatham cottage
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.9 out of 5 average rating, 164 reviews
Top guest favourite
Tiny home in Eastham
Breezy Bay Cottage in the Pines
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chatham
Chatham Cottage - Walk to Beach!
3 bedrooms, 4 beds, 1 bathroom
1–6 Jan
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Flat in Chatham
Bright sunny condo in Chatham!
2 bedrooms, 2 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Chatham
Amazing Location! Chatham Center, Walk to Beach!
3 bedrooms, 4 beds, 4 bathrooms
4–9 Oct
4.93 out of 5 average rating, 29 reviews
Home in Chatham
Four Shore: Walk to town and Oyster Pond Beach
4 bedrooms, 6 beds, 4 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Cottage in Dennis Port
Cape Cod Cottage 3/4 Mile from the Beach
1 queen bed, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 203 reviews
Top guest favourite
Home in Chatham
Walk to the Beach from a Family-Friendly Home in Chatham
3 bedrooms, 6 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 86 reviews
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 116 reviews
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
3 bedrooms, 4 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 41 reviews
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Sept