Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
8 beds
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
10 beds
13–18 Sept
4.88 out of 5 average rating, 56 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
3 beds
28 Aug – 4 Sept
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
4 beds
24–29 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
5 beds
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Home in Chatham
Three Chimneys
On Lighthouse Beach
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
7 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Superhost
Home in Chatham
Great location, Dog Friendly, Central AC!
8 beds
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
5 beds
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
3 beds
22–27 Sept
5.0 out of 5 average rating, 7 reviews
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
4 beds
22–29 Aug
Home in Chatham
Sarah-N-Dipity: Cozy Cottage Near Ridgevale Beach
3 beds
14–19 Sept
Top guest favourite
Home in Chatham
Close to Beach, Dog Friendly, Chatham Cottage
3 beds
22–29 Aug
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Chatham
Ocean Views, AC, Walk to Beach! Fully Renovated.
Sea and river views
15–22 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham MA
8 beds
15–20 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Chatham Family Vacation
4 beds
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Home in Chatham
Thinking of Summer Already? - Book Now Summer '26
6 beds
25–30 Sept
4.99 out of 5 average rating, 71 reviews