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Search results; Over 1,000 homes in Chatham

Top guest favourite
Apartment in Chatham
Chatham Condo with private entrance
2 bedrooms, 3 beds, 2 private bathrooms
29 Aug – 4 Sept
,
4.94 out of 5 average rating, 67 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
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
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
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
SurfShack in Chatham
3 bedrooms, 5 beds
5–11 Sept
4.97 out of 5 average rating, 72 reviews
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
Chatham Family Retreat w/ Game Room & Porch
3 bedrooms, 8 beds
22–29 Aug
5.0 out of 5 average rating, 33 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, 7 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds
15–20 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Thinking of Summer Already? - Book Now Summer '26
3 bedrooms, 6 beds
25–30 Sept
4.99 out of 5 average rating, 71 reviews
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds
19–24 Sept
Top guest favourite
Home in Chatham
Ocean Views, AC, Walk to Beach! Fully Renovated.
3 bedrooms, 4 beds
15–22 Aug
5.0 out of 5 average rating, 10 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
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
Chatham Family Vacation
3 bedrooms, 4 beds
12–17 Sept
4.95 out of 5 average rating, 44 reviews
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5 bedrooms, 5 beds
22–27 Aug
5.0 out of 5 average rating, 3 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