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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
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4.99 out of 5 average rating, 70 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
Guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds
9–14 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Chatham
Cozy Cottage
1 bedroom, 1 queen bed
4–9 Nov
4.97 out of 5 average rating, 295 reviews
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds
28 Aug – 4 Sept
4.97 out of 5 average rating, 173 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
The Boarding House. Steps from Ice Cream Shop
4 bedrooms, 5 beds
11–18 Jul
5.0 out of 5 average rating, 55 reviews
Superhost
Home in Chatham
Central AC, Game Room, Dog-Friendly!
3 bedrooms, 4 beds
25–30 Sept
Home in Harwich
Walk to Beach & Town | Renovated Retreat
2 bedrooms, 3 beds
15–22 Aug
New place to stay
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
Home in Chatham
Cape Cod Private Retreat
3 bedrooms, 8 beds
10–17 Jul
4.89 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chatham
Down Thyme, Chatham, MA
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Chatham
4BR in Chatham. Walk to Town & Chatham As Games!
4 bedrooms, 6 beds
22–28 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Chatham
Chatham with Private Beach
2 bedrooms, 3 beds
15–22 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Chatham
Walkable to Downtown Chatham Home with Bikes
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 13 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
Downtown Chatham Walk to Everything: 4 Bedroom+
4 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chatham
Coastal Chic meets Antique Charm
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Home in Chatham
5 BR-Property-Chatham in-Town & Oyster Beach Inlet
5 bedrooms, 6 beds
12–17 Oct
4.89 out of 5 average rating, 53 reviews