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Search results; Over 1,000 homes in Chatham

Top guest favourite
Apartment in Chatham
Private Pied-a-Terre, in-village hidden Oasis.
1 bedroom, 1 bed, 1 private bathroom
10–15 Oct
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4.97 out of 5 average rating, 394 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds
14–19 Sept
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
5 bedrooms, 7 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds
24–29 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds
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
26 Sept – 1 Oct
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
3 bedrooms, 5 beds
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
5 bedrooms, 10 beds
13–18 Sept
4.88 out of 5 average rating, 56 reviews
Home in Chatham
Chatham Home near Downtown
2 bedrooms, 3 beds
22–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham Home, Walk to Beach and Town
3 bedrooms, 5 beds
29 May – 5 Jun
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chatham
Dog Friendly, Game Room, Central AC!
3 bedrooms, 5 beds
19–24 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chatham
Close to Beach, Dog Friendly, Chatham Cottage
2 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Chatham
*New* ~ near Jackknife Beach/Wequassett/Gameroom
3 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in South Chatham
Wrap-Around Porch Mins. to Beach!
2 bedrooms, 4 beds
10–15 Oct
4.86 out of 5 average rating, 96 reviews
Home in Chatham
Spacious 2 family home! Plenty of room!
7 bedrooms, 9 beds
23–28 Aug
Guest favourite
Home in Chatham
Sun Drenched, 0.2 mi to Bike Path, <1mi to Beach
3 bedrooms, 6 beds
4–9 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Chatham
Meadow + Main
3 bedrooms, 5 beds
11–16 Oct
5.0 out of 5 average rating, 17 reviews