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, 68 reviews
Home in Chatham
Relaxing Cape Escape • Walk to Beach • 6 Beds
4 bedrooms, 6 beds, 3 bathrooms
17–22 Jul
5.0 out of 5 average rating, 4 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
7–14 Jul
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Chatham
Close to Beach Renovated Dog Friendly Cape Cottage
2 bedrooms, 3 beds, 1 bathroom
11–18 Jul
4.97 out of 5 average rating, 31 reviews
Superhost
Home in Chatham
Chatham Home overlooking Cranberry Bog
5 bedrooms, 5 beds, 4.5 bathrooms
22–27 Aug
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, 19 reviews
Top guest favourite
Home in Chatham
The Chatham Bars White Foam House Steps From Beach
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Chatham
Chatham condo steps to town beaches+CBI+Squire
2 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Chatham
4BR in Chatham. Walk to Town & Chatham As Games!
4 bedrooms, 6 beds, 2 bathrooms
25–31 Jul
5.0 out of 5 average rating, 5 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
Home in Chatham
Sun Drenched, 0.2 mi to Bike Path, <1mi to Beach
3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
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
Home in Chatham
Historic 1850 Chatham home.
2 bedrooms, 5 beds, 1 bathroom
21–26 Jul
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Chatham
No Pet Fee, Waterfront, Fenced Yard, Close to Town
5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Home in Chatham
Three Chimneys
4 bedrooms, 4 beds, 1.5 bathrooms
18–23 Jul
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, 54 reviews
Top guest favourite
Home in Chatham
Secluded Chatham Cape Cod House Stage Harbor Area
3 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.93 out of 5 average rating, 110 reviews
Guest favourite
Home in Chatham
Cape Cod Private Retreat
3 bedrooms, 8 beds, 1.5 bathrooms
3–10 Jul
4.89 out of 5 average rating, 28 reviews