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Search results; Over 1,000 homes in Chatham

Guest favourite
Cottage in Chatham
Chit-Chat Cottage on White pond, near DT/beaches.
2 bedrooms, 3 beds, 1 private bathroom
28 Sept – 3 Oct
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4.96 out of 5 average rating, 70 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
4.97 out of 5 average rating, 102 reviews, 5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
Home in Chatham
Four Shore: Walk to town and Oyster Pond Beach
New place to stay, 4 bedrooms, 6 beds, 4 bathrooms
22–27 Aug
Top guest favourite
Home in Chatham
Brand new, in-town Chatham home
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
4.93 out of 5 average rating, 41 reviews, 3 bedrooms, 4 beds, 1 bathroom
22–27 Aug
Top guest favourite
Home in Chatham
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
23–30 Aug
Home in Chatham
Three Chimneys
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 5 beds, 1.5 bathrooms
24–29 Aug
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
4.98 out of 5 average rating, 63 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
Home in Chatham
5 BR-Property-Chatham in-Town & Oyster Beach Inlet
4.89 out of 5 average rating, 54 reviews, 5 bedrooms, 6 beds, 2.5 bathrooms
12–17 Oct
Top guest favourite
Home in Chatham
Luxury Home- Chatham Center- Walk to Town + Beach
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 3 beds, 3 bathrooms
22–29 Aug
Top guest favourite
Home in Eastham
10 min walk to Beach - Amazing View & Huge Deck
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Oct
Top guest favourite
Home in Chatham
The Boarding House. Steps from Ice Cream Shop
5.0 out of 5 average rating, 55 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
22–29 Aug
Cabin in Chatham
Pleasant Forest Shores - Cottage #1 - S Chatham
4.7 out of 5 average rating, 24 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Sept
Top guest favourite
Home in Chatham
Close to Beach, Dog Friendly, Chatham Cottage
4.97 out of 5 average rating, 33 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–29 Aug
Home in Chatham
Chatham Home near Downtown
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–29 Aug
Guest favourite
Home in Chatham
Dog Friendly, Game Room, Central AC!
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
19–24 Oct
Top guest favourite
Home in Harwich
Beautiful Home Near the Ocean.
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct
Top guest favourite
Home in Chatham
Central AC, Pet-friendly, Walk to water & town!
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Guest house in Dennis Port
Almond - Check In 12:00 pm - On the Beach by 12:15
4.94 out of 5 average rating, 557 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct