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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
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
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
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
13–20 Jul
4.94 out of 5 average rating, 16 reviews
Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
5 bedrooms, 10 beds, 4 bathrooms
13–18 Sept
4.88 out of 5 average rating, 56 reviews
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
3 bedrooms, 8 beds, 3.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Chatham
Chatham House Near Town and Beach
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 Sept
4.98 out of 5 average rating, 95 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
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
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Home in Chatham
Water View Chatham Retreat: Bike Trail+White Pond
3 bedrooms, 3 beds, 3 bathrooms
24–29 Aug
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, 145 reviews
Home in Chatham
Spacious 2 family home! Plenty of room!
7 bedrooms, 9 beds, 6 bathrooms
17–24 Aug
New place to stay
Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 4 Sept
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 58 reviews
Home in Chatham
Three Chimneys
5 bedrooms, 5 beds, 1.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 29 reviews