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Search results; Over 1,000 homes in Chatham

Top guest favourite
Apartment in Chatham
Private Beach in Chatham - Sleeps 5
2 bedrooms, 3 beds, 1 private bathroom
19–24 Oct
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4.88 out of 5 average rating, 135 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
4.97 out of 5 average rating, 295 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Nov
Top guest favourite
Room in Chatham
Nantucket House of Chatham - Chatham Room
4.95 out of 5 average rating, 190 reviews, 1 king bed, 1 bathroom
16–21 Oct
Cabin in Chatham
Pleasant Forest Shores - Cottage #1 - S Chatham
4.7 out of 5 average rating, 24 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Sept
Top guest favourite
Flat in Chatham
Chatham Studio- short walk to beach
4.96 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Sept
Guest favourite
Cottage in Chatham
Forbes, a South Chatham cottage
4.9 out of 5 average rating, 164 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
Top guest favourite
Tiny home in Eastham
Breezy Bay Cottage in the Pines
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Chatham
Chatham Cottage - Walk to Beach!
5.0 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 1 bathroom
1–6 Jan
Top guest favourite
Flat in Chatham
Bright sunny condo in Chatham!
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 2 bathrooms
31 Aug – 5 Sept
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
4.93 out of 5 average rating, 41 reviews, 3 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Home in Chatham
Four Shore: Walk to town and Oyster Pond Beach
New place to stay, 4 bedrooms, 6 beds, 4 bathrooms
22–27 Aug
Guest favourite
Home in Chatham
Amazing Location! Chatham Center, Walk to Beach!
4.93 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 4 bathrooms
4–9 Oct
Top guest favourite
Home in Chatham
Walk to the Beach from a Family-Friendly Home in Chatham
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 6 beds, 2 bathrooms
2–7 Oct
Top guest favourite
Cottage in Dennis Port
Cape Cod Cottage 3/4 Mile from the Beach
4.93 out of 5 average rating, 203 reviews, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
Top guest favourite
Holiday home in Chatham
Beautiful Downtown Chatham 1 Bed, Near Oyster Pond
5.0 out of 5 average rating, 72 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
4.97 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Apartment in Chatham
Private Pied-a-Terre, in-village hidden Oasis.
4.97 out of 5 average rating, 391 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Oct