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Search results; Over 1,000 homes in Chatham

Top guest favourite
Home in Chatham
Downtown Chatham Home w/ Patio - Near Oyster Pond
3 bedrooms, 4 beds, 2.5 private bathrooms
6–11 Sept
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5.0 out of 5 average rating, 52 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
Superhost
Home in Chatham
4BR Chatham | Lake Access & Vaulted Sunroom
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Chatham
Oceanfront Chatham Village Home
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 102 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
Brand new, in-town Chatham home
3 bedrooms, 5 beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
1–6 Jul
4.93 out of 5 average rating, 15 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
16–23 Aug
Top guest favourite
Home in Chatham
Historic 1850 Chatham home.
2 bedrooms, 5 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 17 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
Superhost
Home in Chatham
Dog Friendly, Game Room, Central AC!
3 bedrooms, 5 beds, 3.5 bathrooms
19–24 Oct
Top guest favourite
Home in Eastham
10 min walk to Beach - Amazing View & Huge Deck
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Chatham
Town Center WalkTo All Stores Full Reno 2026 2Bdrm
2 bedrooms, 3 beds, 1 bathroom
22–27 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
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
5–10 Oct
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
Unique Oyster Pond 3bd-2ba home close to downtown.
3 bedrooms, 5 beds, 2 bathrooms
7–13 Sept
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Chatham
*New* 3Bd/3B Jackknife Beach/Wequassett/Gameroom
3 bedrooms, 5 beds, 3 bathrooms
4–11 Jul
New place to stay
Guest favourite
Home in Chatham
Pond Views-Firepit-Game Room-Beach Access-Kayaks
4 bedrooms, 5 beds, 3.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cottage in Chatham
Cottage with Views of Nantucket Sound
3 bedrooms, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.92 out of 5 average rating, 39 reviews