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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, 391 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 103 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Chatham
New! Luxury Home near town, beach, lake access!
4 bedrooms, 6 beds, 2.5 bathrooms
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Harwich
Beautiful Home Near the Ocean.
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Chatham
Dog Friendly, Game Room, Central AC!
3 bedrooms, 5 beds, 3.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 173 reviews
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
3 bedrooms, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.93 out of 5 average rating, 42 reviews
Home in Harwich
Lakefront Escape, Private Beach, Stunning Views!
4 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Chatham
*New* ~ near Jackknife Beach/Wequassett/Gameroom
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Home in Chatham
5 BR-Property-Chatham in-Town & Oyster Beach Inlet
5 bedrooms, 6 beds, 2.5 bathrooms
12–17 Oct
4.89 out of 5 average rating, 54 reviews
Top guest favourite
Home in Chatham
Downtown Chatham Home w/ Patio - Near Oyster Pond
3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 61 reviews
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chatham
Thinking of Summer Already? - Book Now Summer '26
3 bedrooms, 6 beds, 2 bathrooms
25–30 Sept
4.99 out of 5 average rating, 71 reviews