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Search results; Over 1,000 homes in Chatham

Top guest favourite
Apartment in Chatham
Private Pied-a-Terre, in-village hidden Oasis.
1 bedroom, 1 bed, 1 private bathroom
10–15 Oct
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4.97 out of 5 average rating, 392 reviews
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
Guest favourite
Guest suite in Chatham
Waterfront Suite on Emery Pond
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 270 reviews
Top guest favourite
Room in Chatham
Nantucket House of Chatham - Chatham Room
1 king bed, 1 bathroom
16–21 Oct
4.95 out of 5 average rating, 190 reviews
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
Top guest favourite
Flat in Chatham
Chatham Studio- short walk to beach
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
4.96 out of 5 average rating, 24 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, 173 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Dennis Port
Almond - Check In 12:00 pm - On the Beach by 12:15
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 560 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, 116 reviews
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 297 reviews
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
2 bedrooms, 4 beds, 1 bathroom
12–17 Oct
4.92 out of 5 average rating, 205 reviews
Top guest favourite
Home in Chatham
Charming Chatham Home! Less than Mile To Beach !
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 96 reviews
Top guest favourite
Apartment in Chatham
Condo on Lighthouse Beach in Chatham
2 bedrooms, 3 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Dennis Port
Cape Cod Cottage 3/4 Mile from the Beach
1 queen bed, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 204 reviews
Cabin in Chatham
Pleasant Forest Shores - Cottage #1 - S Chatham
1 bedroom, 2 single beds, 1 bathroom
18–23 Sept
4.7 out of 5 average rating, 24 reviews
Home in Chatham
Four Shore: Walk to town and Oyster Pond Beach
4 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Home in Chatham
Central AC, Pet-friendly, Walk to water & town!
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 40 reviews