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Search results; Over 1,000 homes in Chatham

Guest favourite
Cottage in Chatham
Renovated Chatham Windmill! Walk to Beach/Town!
1 bedroom, 1 bed, 1 private bathroom
19–24 Oct
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4.95 out of 5 average rating, 83 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
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
Superhost
Home in Chatham
Great location, Dog Friendly, Central AC!
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 8 beds, 4 bathrooms
5–10 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
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
Home in Chatham
Three Chimneys
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 1.5 bathrooms
24–29 Aug
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, 8 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
28 Jul – 4 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
Coastal Chic meets Antique Charm
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds, 4 bathrooms
19–24 Sept
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
17–22 Jul
Home in Chatham
Chatham Home near Downtown
2 bedrooms, 3 beds, 1 bathroom
22–29 Aug
Top guest favourite
Home in Chatham
Chatham Family Vacation
4.95 out of 5 average rating, 44 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 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
Top guest favourite
Home in Chatham
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Chatham
Newly Built Home | 5 Min Walk to Ridgevale Beach
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept