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Search results; Over 1,000 homes in Chatham

Top guest favourite

Home in Chatham

Oceanfront Chatham Village Home

8 beds

4–9 Oct

$6,790 SGD for 5 nights

4.97 out of 5 average rating, 102 reviews

Luxe

Home in Chatham

Steps to Beach + Game Room + Porch | Coastal Haven

10 beds

13–18 Sept

$13,094 SGD for 5 nights

4.88 out of 5 average rating, 56 reviews

Top guest favourite

Home in Chatham

The Chatham Bars White Foam House Steps From Beach

4 beds

24–29 Oct

$4,998 SGD for 5 nights

5.0 out of 5 average rating, 29 reviews

Top guest favourite

Home in Chatham

Brand new, in-town Chatham home

5 beds

5–10 Sept

$5,573 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Home in Chatham

No Pet Fee, Waterfront, Fenced Yard, Close to Town

7 beds

27 Sept – 2 Oct

$4,049 SGD for 5 nights

4.98 out of 5 average rating, 62 reviews

Top guest favourite

Home in Chatham

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

3 beds

22–27 Sept

$3,936 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Chatham

SurfShack in Chatham

5 beds

5–11 Sept

$8,845 SGD for 6 nights

4.97 out of 5 average rating, 72 reviews

Home in Chatham

All-New Coastal Luxury Near CBI & Beaches

Kayak

16–23 Aug

$16,447 SGD for 7 nights

Top guest favourite

Home in Chatham

Beachfront Charmer! Newly Renovated.

5 beds

26–31 Oct

$2,233 SGD for 5 nights

4.97 out of 5 average rating, 116 reviews

Top guest favourite

Home in Chatham

Chatham Family Retreat w/ Game Room & Porch

8 beds

22–29 Aug

$8,480 SGD for 7 nights

5.0 out of 5 average rating, 33 reviews

Top guest favourite

Home in Chatham

Ocean Views, AC, Walk to Beach! Fully Renovated.

Sea and river views

15–22 Aug

$12,818 SGD for 7 nights

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Home in Chatham

Chatham Family Vacation

4 beds

12–17 Sept

$2,421 SGD for 5 nights

4.95 out of 5 average rating, 44 reviews

Superhost

Home in Chatham

Waterfront Escape, Game Room, Dog Friendly!

9 beds

19–24 Sept

Superhost

Home in Chatham

Chatham Home overlooking Cranberry Bog

5 beds

22–27 Aug

$8,354 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Flat in Chatham

The Knoll

3 beds

7–12 Sept

$1,673 SGD for 5 nights

4.96 out of 5 average rating, 289 reviews

Top guest favourite

Home in Chatham

Thinking of Summer Already? - Book Now Summer '26

6 beds

25–30 Sept

$3,445 SGD for 5 nights

4.99 out of 5 average rating, 71 reviews

Top guest favourite

Home in Chatham

Beautiful Chatham MA

8 beds

14–19 Jul

$5,265 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chatham

Newly Built Home | 5 Min Walk to Ridgevale Beach

4 beds

20–25 Sept

$5,633 SGD for 5 nights

4.96 out of 5 average rating, 49 reviews