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Search results; Over 1,000 homes in Chatham

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
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4.97 out of 5 average rating, 173 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, 116 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
4–9 Nov
4.97 out of 5 average rating, 295 reviews
Guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
9–14 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
2 bedrooms, 4 beds, 1 bathroom
12–17 Oct
4.92 out of 5 average rating, 205 reviews
Top guest favourite
Home in Chatham
The Boarding House. Steps from Ice Cream Shop
4 bedrooms, 5 beds, 1.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 55 reviews
Superhost
Home in Chatham
Waterfront Escape, Game Room, Dog Friendly!
6 bedrooms, 9 beds, 4 bathrooms
19–24 Sept
New place to stay
Top guest favourite
Guest suite in Harwich
Romantic getaway suite
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 656 reviews
Top guest favourite
Home in Chatham
Historic 1850 Chatham home.
2 bedrooms, 5 beds, 1 bathroom
21–26 Jul
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Home in Harwich
Walk to Beach & Town | Renovated Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
15–22 Aug
New place to stay
Top guest favourite
Home in Harwich
Secluded Cape Home | Fire Pit & Hammock
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Chatham
4BR in Chatham. Walk to Town & Chatham As Games!
4 bedrooms, 6 beds, 2 bathrooms
22–28 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Sept
Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds, 1 bathroom
15–22 Aug
5.0 out of 5 average rating, 10 reviews
Home in Harwich
300ft to Red River Beach / Roof Deck / AC
3 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
New place to stay
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 7 reviews