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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, 82 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
4.97 out of 5 average rating, 102 reviews, 5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
4.98 out of 5 average rating, 62 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
4.88 out of 5 average rating, 56 reviews, 5 bedrooms, 10 beds, 4 bathrooms
13–18 Sept
Top guest favourite
Home in Chatham
Chatham House Near Town and Beach
4.98 out of 5 average rating, 94 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Flat in Chatham
The Knoll
4.96 out of 5 average rating, 289 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
4.92 out of 5 average rating, 205 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 Oct
Guest favourite
Home in Chatham
4BR in Chatham. Walk to Town & Chatham As Games!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 2 bathrooms
22–28 Aug
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
Home in Chatham
Water View Chatham Retreat: Bike Trail+White Pond
3 bedrooms, 3 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Home in Chatham
Chatham Family Vacation
4.95 out of 5 average rating, 43 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
4.97 out of 5 average rating, 145 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
Top guest favourite
Home in Chatham
Bookends and Pencil Me Inn
5.0 out of 5 average rating, 35 reviews, 3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
New place to stay, 6 bedrooms, 9 beds, 4 bathrooms
19–24 Sept
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Rooms in Chatham
Tina's Culdesac B&B Sleeps 4 w/ Breakfast
5.0 out of 5 average rating, 34 reviews, 2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept