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Search results; Over 1,000 homes in Chatham

Guest favourite
Apartment in Chatham
Private Beach in Chatham - Sleeps 5
2 bedrooms, 3 beds, 1 private bathroom
5–10 Oct
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4.88 out of 5 average rating, 131 reviews
Guest favourite
Home in Chatham
Beautiful Chatham MA
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 8 beds, 2 bathrooms
6–12 Jul
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
6–11 Jul
Home in Chatham
Hydrangea Haven: Your Homey Chatham Getaway
2 bedrooms, 4 beds, 2 bathrooms
15–22 Aug
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Home in Chatham
Historic 1850 Chatham home.
4.94 out of 5 average rating, 18 reviews, 2 bedrooms, 5 beds, 1 bathroom
21–26 Jul
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Cottage in Chatham
Cozy Cottage
4.97 out of 5 average rating, 295 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Nov
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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
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Home in Chatham
Down Thyme, Chatham, MA
5.0 out of 5 average rating, 20 reviews, 2 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
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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
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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
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Rooms in Chatham
Tina's Culdesac B&B Sleeps 4 w/ Breakfast
5.0 out of 5 average rating, 34 reviews, 2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
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Home in Harwich
Secluded Cape Home | Fire Pit & Hammock
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
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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
11–18 Jul
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Home in Chatham
Chatham Family Vacation
4.95 out of 5 average rating, 42 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
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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
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Flat in Chatham
The Knoll
4.96 out of 5 average rating, 289 reviews, 2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
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Apartment in Chatham
Chatham Condo with private entrance
4.94 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 4 Sept
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Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
4.98 out of 5 average rating, 62 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
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Home in Chatham
Now open Sept 22-30 Town Center 2026 Total Reno
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Sept