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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, 81 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, 16 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
Oceanfront Chatham Village Home
5 bedrooms, 8 beds
6–11 Jul
4.97 out of 5 average rating, 102 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
Home in Chatham
Three Chimneys
5 bedrooms, 5 beds
18–23 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5 bedrooms, 5 beds
22–27 Aug
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
3 bedrooms, 5 beds
19–24 Sept
New place to stay
Top guest favourite
Home in Chatham
Now open Sept 22-30 Town Center 2026 Total Reno
2 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 7 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
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds
15–22 Aug
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds
16–23 Aug
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds
14–19 Sept
4.97 out of 5 average rating, 143 reviews
Home in Harwich
Lakefront Escape, Private Beach, Kayak, Swim Views
4 bedrooms, 7 beds
12–18 Jul
New place to stay
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds
5–10 Oct
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Chatham
Downtown Chatham Home w/ Patio - Near Oyster Pond
3 bedrooms, 4 beds
6–11 Sept
5.0 out of 5 average rating, 54 reviews