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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
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
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
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
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
New place to stay, 6 bedrooms, 9 beds, 4 bathrooms
19–24 Sept
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
Home in Chatham
Three Chimneys
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 1.5 bathrooms
18–23 Jul
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5 bedrooms, 5 beds, 4.5 bathrooms
22–27 Aug
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
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
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Top guest favourite
Home in Chatham
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
9–14 Jul
Home in Chatham
Coastal Fun in Chatham – Your Cape Cod Escape
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
4.97 out of 5 average rating, 173 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 4 Sept
Top guest favourite
Home in Chatham
Walkable to Downtown Chatham Home with Bikes
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1 bathroom
28 Sept – 3 Oct
Home in Chatham
IDEAL LOCATION. WATER VIEW,BEACH, WALK TO TOWN
4.67 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
18–25 Jul
Top guest favourite
Home in Chatham
Meadow + Main
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept