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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
Thinking of Summer Already? - Book Now Summer '26
3 bedrooms, 6 beds, 2 private bathrooms
25–30 Sept
,
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds
12–19 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Harwich
Romantic getaway suite
1 bedroom, 2 beds
4–9 Oct
4.99 out of 5 average rating, 656 reviews
Top guest favourite
Home in Chatham
Quaint Downtown Chatham Home
2 bedrooms, 4 beds
12–17 Oct
4.92 out of 5 average rating, 205 reviews
Top guest favourite
Home in Chatham
Chatham Charmer
2 bedrooms, 3 beds
5–10 Oct
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Home in Chatham
The Boarding House. Steps from Ice Cream Shop
4 bedrooms, 5 beds
25 Jul – 1 Aug
5.0 out of 5 average rating, 55 reviews
Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed
8–13 Nov
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds
22–29 Aug
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Top guest favourite
Home in Chatham
Beachfront Charmer! Newly Renovated.
3 bedrooms, 5 beds
26–31 Oct
4.97 out of 5 average rating, 116 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Harwich
Secluded Cape Home | Fire Pit & Hammock
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Flat in Chatham
Chatham condo steps to town beaches+CBI+Squire
2 bedrooms, 4 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds
25–30 Sept
Top guest favourite
Apartment in Chatham
Two bedroom condo close to beach
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 58 reviews
Guest favourite
Home in Chatham
Chatham Gem: 3BR Near Downtown & Ballfield
3 bedrooms, 4 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds
22–27 Sept
5.0 out of 5 average rating, 7 reviews