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Search results; Over 1,000 homes in Chatham

Top guest favourite

Guest suite in Chatham

Spacious Moonhouse Studio - Chatham

1 bedroom, 2 beds, 1 private bathroom

1–6 Jan

$2,012 SGD for 5 nights

,

4.99 out of 5 average rating, 139 reviews

Top guest favourite

Cottage in Chatham

Cozy Cottage

1 bedroom, 1 queen bed

8–13 Nov

$1,702 SGD for 5 nights

Pay $0 today

Free cancellation

4.97 out of 5 average rating, 295 reviews

Top guest favourite

Room in Chatham

Nantucket House of Chatham - Chatham Room

1 king bed

16–21 Oct

$1,277 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 190 reviews

Cabin in Chatham

Pleasant Forest Shores - Cottage #1 - S Chatham

1 bedroom, 2 single beds

18–23 Sept

$760 SGD for 5 nights

4.7 out of 5 average rating, 24 reviews

Top guest favourite

Flat in Chatham

Chatham Studio- short walk to beach

1 bedroom, 2 beds

25–30 Sept

$962 SGD for 5 nights

4.96 out of 5 average rating, 23 reviews

Guest favourite

Cottage in Chatham

Forbes, a South Chatham cottage

2 bedrooms, 3 beds

13–18 Oct

$1,178 SGD for 5 nights

4.9 out of 5 average rating, 164 reviews

Top guest favourite

Tiny home in Eastham

Breezy Bay Cottage in the Pines

1 bedroom, 2 beds

2–7 Aug

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Chatham

Chatham Cottage - Walk to Beach!

3 bedrooms, 4 beds

1–6 Jan

$1,900 SGD for 5 nights

5.0 out of 5 average rating, 46 reviews

Top guest favourite

Flat in Chatham

Bright sunny condo in Chatham!

2 bedrooms, 2 beds

31 Aug – 5 Sept

$2,584 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Guest favourite

Home in Chatham

Amazing Location! Chatham Center, Walk to Beach!

3 bedrooms, 4 beds

4–9 Oct

$3,534 SGD for 5 nights

4.93 out of 5 average rating, 29 reviews

Home in Chatham

Four Shore: Walk to town and Oyster Pond Beach

4 bedrooms, 6 beds

22–27 Aug

$5,448 SGD for 5 nights

New place to stay

Top guest favourite

Home in Chatham

Walk to the Beach from a Family-Friendly Home in Chatham

3 bedrooms, 6 beds

2–7 Oct

$3,876 SGD for 5 nights

5.0 out of 5 average rating, 86 reviews

Top guest favourite

Cottage in Dennis Port

Cape Cod Cottage 3/4 Mile from the Beach

1 queen bed

17–22 Aug

$1,710 SGD for 5 nights

Pay $0 today

Free cancellation

4.93 out of 5 average rating, 203 reviews

Top guest favourite

Home in Chatham

Town Center-Steps to Shops-Walk To Beach-2026 Reno

2 bedrooms, 3 beds

22–27 Sept

$4,428 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Home in Harwich

300ft to Red River Beach / Roof Deck / AC

3 bedrooms, 5 beds

19–24 Sept

$5,016 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cottage in Chatham

Cottage with Views of Nantucket Sound

3 bedrooms, 4 beds

22–27 Aug

$2,684 SGD for 5 nights

4.93 out of 5 average rating, 41 reviews

Top guest favourite

Holiday home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

1 bedroom, 1 queen bed

28 Aug – 2 Sept

$4,571 SGD for 5 nights

5.0 out of 5 average rating, 72 reviews

Top guest favourite

Home in Chatham

Beachfront Charmer! Newly Renovated.

3 bedrooms, 5 beds

26–31 Oct

$2,218 SGD for 5 nights

4.97 out of 5 average rating, 116 reviews

Top guest favourite

Home in Brewster

Renovated Beach House, Central AC, Private Ponds

3 bedrooms, 4 beds

1–6 Jan

Book early to save

5.0 out of 5 average rating, 68 reviews