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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, 68 reviews
Guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
6–12 Jul
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
6–11 Jul
4.97 out of 5 average rating, 102 reviews
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
15–22 Aug
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
4–9 Nov
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Home in Chatham
The Boarding House. Steps from Ice Cream Shop
4 bedrooms, 5 beds, 1.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Home in Chatham
Downtown Chatham Walk to Everything: 4 Bedroom+
4 bedrooms, 5 beds, 2.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Guest suite in Harwich
Romantic getaway suite
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 656 reviews
Guest favourite
Home in Chatham
Chatham Gem: 3BR Near Downtown & Ballfield
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 5 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
Rooms in Chatham
Tina's Culdesac B&B Sleeps 4 w/ Breakfast
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Chatham
The Knoll
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Top guest favourite
Home in Chatham
Chatham Family Vacation
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Apartment in Chatham
Chatham Condo with private entrance
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 4 Sept
4.94 out of 5 average rating, 67 reviews
Top guest favourite
Home in Harwich
Secluded Cape Home | Fire Pit & Hammock
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Chatham
Historic 1850 Chatham home.
2 bedrooms, 5 beds, 1 bathroom
21–26 Jul
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Home in Chatham
Now open Sept 22-30 Town Center 2026 Total Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 7 reviews