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Search results; Over 1,000 homes in Chatham

Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 bed, 1 private bathroom
8–13 Nov
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4.97 out of 5 average rating, 295 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham MA
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 8 beds, 2 bathrooms
12–19 Jul
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
4.92 out of 5 average rating, 205 reviews, 2 bedrooms, 4 beds, 1 bathroom
12–17 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
25 Jul – 1 Aug
Top guest favourite
Guest suite in Harwich
Romantic getaway suite
4.99 out of 5 average rating, 656 reviews, 1 bedroom, 2 beds, 1 bathroom
4–9 Oct
Guest favourite
Flat in Chatham
Chatham with Private Beach
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
22–29 Aug
Top guest favourite
Home in Chatham
Chatham Charmer
4.99 out of 5 average rating, 192 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
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
Top guest favourite
Flat in Chatham
The Knoll
4.96 out of 5 average rating, 289 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Chatham
Chatham Gem: 3BR Near Downtown & Ballfield
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 5 Sept
Top guest favourite
Home in Chatham
Downtown Chatham Walk to Everything: 4 Bedroom+
5.0 out of 5 average rating, 28 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Harwich
Secluded Cape Home | Fire Pit & Hammock
5.0 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Sept
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
4.97 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
26–31 Oct
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
4.95 out of 5 average rating, 58 reviews, 2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
Guest favourite
Flat in Chatham
Chatham condo steps to town beaches+CBI+Squire
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept