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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 shared bathrooms
28 Aug – 4 Sept
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4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 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
5 bedrooms, 10 beds
13–18 Sept
4.88 out of 5 average rating, 56 reviews
Superhost
Home in Chatham
Great location, Dog Friendly, Central AC!
6 bedrooms, 8 beds
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 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
3 bedrooms, 5 beds
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Home in Chatham
Three Chimneys
5 bedrooms, 5 beds
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
5 bedrooms, 7 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 8 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds
28 Jul – 4 Aug
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds
26–31 Oct
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds
17–22 Jul
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds
19–24 Sept
Home in Chatham
Chatham Home near Downtown
2 bedrooms, 3 beds
22–29 Aug
Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds
16–21 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Newly Built Home | 5 Min Walk to Ridgevale Beach
3 bedrooms, 4 beds
20–25 Sept
4.96 out of 5 average rating, 49 reviews