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Search results; Over 1,000 homes in Chatham

Descriptions are based on details hosts provide
Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 shared bathrooms
28 Aug – 4 Sept
,
4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Chatham
Oceanfront with ocean views from every room
5 bedrooms, 8 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Chatham
Town Center-Steps to Shops-Walk To Beach-2026 Reno
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chatham
Waterfront home with direct water access
5 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chatham
Quiet retreat next to conservation land
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 289 reviews
Luxe
Home in Chatham
Steps to Beach + Game Room + Porch | Coastal Haven
5 bedrooms, 10 beds, 4 bathrooms
13–18 Sept
4.88 out of 5 average rating, 56 reviews
Superhost
Home in Chatham
Overlooking a cranberry bog near beaches
6 bedrooms, 8 beds, 4 bathrooms
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chatham
Chatham Family Retreat w/ Game Room & Porch
3 bedrooms, 8 beds, 3.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 33 reviews
Home in Chatham
All-New Coastal Luxury Near CBI & Beaches
3 bedrooms, 4 beds, 2 bathrooms
28 Jul – 4 Aug
Top guest favourite
Home in Chatham
Beautiful Chatham MA
3 bedrooms, 8 beds, 2 bathrooms
15–20 Jul
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Quiet cul-de-sac, one block from downtown
3 bedrooms, 4 beds, 2.5 bathrooms
29 Aug – 5 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Chatham
Renovated Cape Cod home with fire pit
3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 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
Top guest favourite
Apartment in Chatham
Two-story condo with decks near beach
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 58 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
Home in Chatham
Stylish Downtown Chatham Retreat
5 bedrooms, 9 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Home in Chatham
1930s bungalow with a covered porch
3 bedrooms, 5 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Chatham
1850 Greek Revival with original details
2 bedrooms, 5 beds, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 19 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