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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Apartment in Chatham
Private Pied-a-Terre, in-village hidden Oasis.
1 bedroom, 1 bed, 1 private bathroom
24–29 Oct
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4.97 out of 5 average rating, 405 reviews
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Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds
26–31 Oct
4.97 out of 5 average rating, 177 reviews
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Top guest favourite
Home in Chatham
Meadow + Main
3 bedrooms, 5 beds
18–23 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed
8–13 Nov
4.97 out of 5 average rating, 295 reviews
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Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds
26–31 Oct
4.97 out of 5 average rating, 118 reviews
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Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds
24–29 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds
27 Nov – 2 Dec
4.97 out of 5 average rating, 103 reviews
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Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
5 bedrooms, 7 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 65 reviews
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Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds
30 May – 4 Jun
4.96 out of 5 average rating, 310 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
16–21 May
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Chatham
Amazing Location! Chatham Center, Walk to Beach!
3 bedrooms, 4 beds
9–14 Nov
4.93 out of 5 average rating, 29 reviews
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Guest favourite
Home in Chatham
IDEAL LOCATION. WATER VIEW,BEACH, WALK TO TOWN
3 bedrooms, 4 beds
26 Sept – 3 Oct
4.83 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 157 reviews
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Guest favourite
Home in Chatham
Walk to Beach and Town, newly renovated 4/BR
4 bedrooms, 4 beds
20–25 Sept
4.96 out of 5 average rating, 48 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
2–7 Oct
5.0 out of 5 average rating, 87 reviews
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Guest favourite
Home in Chatham
Fall & Winter Cozy Cape Escape, Close to Weddings
3 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 26 reviews