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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
23–28 Sept
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4.95 out of 5 average rating, 88 reviews
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
Top guest favourite
Home in Chatham
Meadow + Main
3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 25 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, 65 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, 14 reviews
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, 49 reviews
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, 117 reviews
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
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
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 156 reviews
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds, 1 bathroom
30 May – 4 Jun
4.96 out of 5 average rating, 310 reviews
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
Guest favourite
Home in Chatham
Fall & Winter Cozy Cape Escape, Close to Weddings
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Chatham
Dog Friendly, Game Room, Central AC!
3 bedrooms, 5 beds, 3.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 9 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, 66 reviews
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
Top guest favourite
Home in Chatham
Downtown Chatham Walk to Everything: 4 Bedroom+
4 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Chatham
Walk to Beach and Town, newly renovated 4/BR
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 48 reviews
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