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Search results; Over 1,000 homes in Chatham

Descriptions are based on details hosts provide
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
,
4.97 out of 5 average rating, 173 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
Two-story glass walls, half mile from beach
4.88 out of 5 average rating, 56 reviews, 5 bedrooms, 10 beds, 4 bathrooms
13–18 Sept
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
Top guest favourite
Home in Chatham
Waterfront home with direct water access
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
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
SurfShack in Chatham
4.97 out of 5 average rating, 72 reviews, 3 bedrooms, 5 beds, 3 bathrooms
5–11 Sept
Top guest favourite
Home in Chatham
Ocean Views, AC, Walk to Beach! Fully Renovated.
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Aug
Top guest favourite
Home in Chatham
Restored 1848 cottage on Main Street
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 8 beds, 3.5 bathrooms
22–29 Aug
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds, 4 bathrooms
19–24 Sept
Top guest favourite
Home in Chatham
Walk to the beach from downtown
4.97 out of 5 average rating, 145 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
22–27 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
Home in Chatham
Newly built, 5-minute walk to beach
4.96 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
20–25 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
14–19 Jul
Top guest favourite
Home in Chatham
New custom build with a fire pit
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
Top guest favourite
Home in Chatham
Thinking of Summer Already? - Book Now Summer '26
4.99 out of 5 average rating, 71 reviews, 3 bedrooms, 6 beds, 2 bathrooms
25–30 Sept