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Search results; Over 1,000 homes in Chatham

Guest favourite
Cottage in Chatham
Cape Cod Classic Cottage Near Forest Beach
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
,
4.93 out of 5 average rating, 196 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
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
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
Chatham House Near Town and Beach
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 8 beds, 3.5 bathrooms
22–29 Aug
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
Flat in Chatham
The Knoll
4.96 out of 5 average rating, 289 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
28 Jul – 4 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
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
The Osprey Nest - Beach house with stunning views
4.97 out of 5 average rating, 173 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 4 Sept
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
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Home in Chatham
Historic 1850 Chatham home.
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 5 beds, 1 bathroom
8–13 Sept
Top guest favourite
Home in Chatham
The Boarding House. Steps from Ice Cream Shop
5.0 out of 5 average rating, 55 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
25 Jul – 1 Aug
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
4.95 out of 5 average rating, 58 reviews, 2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
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
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