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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
Spacious Pet Friendly Cape, Large Yard
4 bedrooms, 6 beds, 2.5 private bathrooms
29 Aug – 5 Sept
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4.95 out of 5 average rating, 101 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
Brand new, in-town Chatham home
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
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
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
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
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
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Top guest favourite
Home in Chatham
Ocean Views, AC, Walk to Beach! Fully Renovated.
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Aug
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
22–27 Aug
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
4.97 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
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
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
Top guest favourite
Home in Chatham
Meadow + Main
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
Home in Chatham
Spacious 2 family home! Plenty of room!
New place to stay, 7 bedrooms, 9 beds, 6 bathrooms
17–24 Aug
Home in Chatham
Coastal Fun in Chatham – Your Cape Cod Escape
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
Home in Harwich
Lakefront Escape, Private Beach, Kayak, Swim Views
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 3 Sept
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