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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
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
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
Oceanfront Chatham Village Home
4.97 out of 5 average rating, 102 reviews, 5 bedrooms, 8 beds, 3 bathrooms
6–11 Jul
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
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
Home in Chatham
Three Chimneys
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 1.5 bathrooms
18–23 Jul
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
New place to stay, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
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
Now open Sept 22-30 Town Center 2026 Total 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
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
15–22 Aug
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Home in Harwich
Lakefront Escape, Private Beach, Kayak, Swim Views
New place to stay, 4 bedrooms, 7 beds, 3.5 bathrooms
12–18 Jul
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
4.97 out of 5 average rating, 143 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
14–19 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
5–10 Oct
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 1 bathroom
26 Sept – 1 Oct
Top guest favourite
Home in Chatham
Spacious Chatham 4BR, Dog OK + Deck + Sleeps 10
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug