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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, 88 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Home in Chatham
SurfShack in Chatham
3 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Home in Chatham
Walk to the Beach from a Family-Friendly Home in Chatham
3 bedrooms, 6 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 117 reviews
Top guest favourite
Home in Chatham
Beautifully renovated home, outdoor space, pets ok
3 bedrooms, 4 beds, 2.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 154 reviews
Top guest favourite
Rooms in Chatham
Tina's Culdesac B&B Sleeps 4 w/ Breakfast
2 bedrooms, 2 king beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 174 reviews
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
2 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 206 reviews
Home in Chatham
Cape Cod Beach House
3 bedrooms, 4 beds, 1.5 bathrooms
5–12 Sept
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
3 bedrooms, 8 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 25 reviews
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Home in Chatham
Walk to beach/Main Street/bike path/dog friendly
2 bedrooms, 2 beds, 1 bathroom
24–29 Sept
4.97 out of 5 average rating, 65 reviews
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Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
16–21 May
5.0 out of 5 average rating, 17 reviews
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Home in Chatham
Charming Chatham Home! Less than Mile To Beach !
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Home in Chatham
Chatham Cape Cod Retreat
4 bedrooms, 5 beds, 2.5 bathrooms
13–20 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Chatham
Oceanview/private beach, Pool, renovated!5bd4bth
5 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 42 reviews
Home in Chatham
Four Shore: Walk to town and Oyster Pond Beach
4 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews