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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
Downtown Chatham Home w/ Patio - Near Oyster Pond
3 bedrooms, 4 beds, 2.5 private bathrooms
12–17 Sept
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5.0 out of 5 average rating, 58 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
Guest favourite
Guest suite in Chatham
Waterfront Suite on Emery Pond
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 271 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, 191 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, 25 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
Top guest favourite
Home in Chatham
Studio cottage in Chatham Ma.
1 bed, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 220 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in Chatham
Private Pied-a-Terre, in-village hidden Oasis.
1 bedroom, 1 queen bed, 1 bathroom
10–15 Oct
4.97 out of 5 average rating, 394 reviews
Top guest favourite
Home in Harwich
Spacious cottage beach Wychmere < 4 min Central AC
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 129 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
Home in Chatham
Close to Beach, Dog Friendly, Chatham Cottage
2 bedrooms, 3 beds, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Dennis Port
Cape Cod Cottage 3/4 Mile from the Beach
1 queen bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 206 reviews
Top guest favourite
Home in Chatham
Charming Chatham Home! Less than Mile To Beach !
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 97 reviews
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Sept
Top guest favourite
Home in Chatham
Central AC, Pet-friendly, Walk to water & town!
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 40 reviews
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 17 reviews