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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds, 2 private bathrooms
26–31 Oct
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4.97 out of 5 average rating, 118 reviews
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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, 177 reviews
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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
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Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
27 Nov – 2 Dec
4.97 out of 5 average rating, 103 reviews
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Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Chatham
Meadow + Main
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Chatham
Stunning Water Views, Walk to Beach, AC, Like New
3 bedrooms, 3 beds, 3.5 bathrooms
17–24 Oct
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Home in Chatham
IDEAL LOCATION. WATER VIEW,BEACH, WALK TO TOWN
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 3 Oct
4.83 out of 5 average rating, 6 reviews
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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, 14 reviews
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Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 50 reviews
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Guest favourite
Home in Chatham
Summer Stay (In-Town)
4 bedrooms, 6 beds, 2.5 bathrooms
4–11 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Chatham
Amazing Location! Chatham Center, Walk to Beach!
3 bedrooms, 4 beds, 4 bathrooms
9–14 Nov
4.93 out of 5 average rating, 29 reviews
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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
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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
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Top guest favourite
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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Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Chatham
New! Luxury Home near town, beach, lake access!
4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
3 bedrooms, 8 beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 38 reviews
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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, 65 reviews