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Search results; Over 1,000 homes in Chatham

Guest favourite
Cottage in Chatham
Renovated Chatham Windmill! Walk to Beach/Town!
1 bedroom, 1 bed, 1 private bathroom
19–24 Oct
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4.95 out of 5 average rating, 83 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 7 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, 62 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
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Top guest favourite
Home in Chatham
Chatham House Near Town and Beach
3 bedrooms, 4 beds
29 Aug – 5 Sept
4.98 out of 5 average rating, 94 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
Guest favourite
Home in Chatham
4BR in Chatham. Walk to Town & Chatham As Games!
4 bedrooms, 6 beds
22–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
2 bedrooms, 4 beds
12–17 Oct
4.92 out of 5 average rating, 205 reviews
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds
14–19 Sept
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Home in Chatham
Water View Chatham Retreat: Bike Trail+White Pond
3 bedrooms, 3 beds
24–29 Aug
Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds
12–17 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chatham
Bookends and Pencil Me Inn
3 bedrooms, 5 beds
4–9 Oct
5.0 out of 5 average rating, 35 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds
16–23 Aug
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds
19–24 Sept
New place to stay
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds
9–14 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 20 reviews