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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
Oceanfront Chatham Village Home
4.97 out of 5 average rating, 102 reviews, 5 bedrooms, 8 beds, 3 bathrooms
4–9 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
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 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
Chatham House Near Town and Beach
4.98 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 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
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 8 beds, 3.5 bathrooms
22–29 Aug
Home in Chatham
Water View Chatham Retreat: Bike Trail+White Pond
3 bedrooms, 3 beds, 3 bathrooms
24–29 Aug
Top guest favourite
Flat in Chatham
The Knoll
4.96 out of 5 average rating, 289 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 4 beds, 3 bathrooms
30 Aug – 4 Sept
Home in Chatham
Sun Drenched, 0.2 mi to Bike Path, <1mi to Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
4.95 out of 5 average rating, 58 reviews, 2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Chatham
Charming Chatham Bungalow-Mins to Downtown+Beaches
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 5 beds, 1 bathroom
22–27 Aug
Top guest favourite
Apartment in Chatham
Chatham Condo with private entrance
4.94 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 4 Sept
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
4.97 out of 5 average rating, 145 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
Top guest favourite
Home in Chatham
Downtown Chatham Home w/ Patio - Near Oyster Pond
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
Top guest favourite
Home in Chatham
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
13–20 Jul