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Search results; Over 1,000 homes in Chatham

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Top guest favourite
Home in Chatham
Open for Fall ‘26 - Best Season on Cape!
3 bedrooms, 6 beds, 2 private bathrooms
12–17 Oct
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4.99 out of 5 average rating, 74 reviews
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Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
23–28 Oct
4.97 out of 5 average rating, 296 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, 178 reviews
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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, 120 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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Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
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, 3 bathrooms
27 Nov – 2 Dec
4.97 out of 5 average rating, 103 reviews
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Top guest favourite
Apartment in Chatham
Storm watch. Warm inside, walk to ocean.
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.97 out of 5 average rating, 409 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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Home in Chatham
Cape Cod Beach House
3 bedrooms, 4 beds, 1.5 bathrooms
17–24 Oct
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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
Dreamcatcher | Luxury Chatham Retreat
2 bedrooms, 5 beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 19 reviews
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Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
5 bedrooms, 10 beds, 4 bathrooms
2–7 Oct
4.88 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Chatham
Chatham House Close to Beaches and Bike Path.
3 bedrooms, 5 beds, 2 bathrooms
1–8 Oct
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.96 out of 5 average rating, 51 reviews
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Guest favourite
Room in Chatham
Private bedroom in high end ocean front home
1 bed, 1.5 bathrooms
1–6 Oct
4.93 out of 5 average rating, 68 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
Chatham Charmer
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 203 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