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Search results; 990 homes in Chester

Top guest favourite

Apartment in Chester

Captain's Quarters - 2 bedroom harbourview condo

2 bedrooms, 2 beds, 1 private bathroom

1–6 Oct

$1,196 SGD for 5 nights

,

4.97 out of 5 average rating, 89 reviews

Top guest favourite

Home in Chester

Endeavour Cottage

2 bedrooms, 3 beds

4–9 Oct

$2,154 SGD for 5 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 87 reviews

Top guest favourite

Home in Chester

White Cottage

4 bedrooms, 4 beds

17–22 Sept

$5,683 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in Chester

The Whale House

3 bedrooms, 3 beds

3–8 Sept

$2,880 SGD for 5 nights

4.99 out of 5 average rating, 69 reviews

Guest favourite

Cottage in Chester

Spectacular 5 Bedroom Spaview Retreat!

5 bedrooms, 5 beds

1–6 Oct

$4,523 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 55 reviews

Guest favourite

Cottage in Chester

Marigold Cottage - 7 bdrms in Chester Village

7 bedrooms, 9 beds

25–30 Aug

$5,353 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 33 reviews

Top guest favourite

Home in Chester

One 12 Queen - EV Charger

3 bedrooms, 4 beds

14–19 Sept

$1,583 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chester Basin

Storybook coastal farmhouse with ocean access

4 bedrooms, 4 beds

6–11 Sept

$2,932 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 30 reviews

Home in Chester

Seaglass House

4 bedrooms, 5 beds

13–20 Jul

$5,115 SGD for 7 nights

Free cancellation

New place to stay

Superhost

Home in Chester

Pine & Sea - Chester's Home for Active Families

3 bedrooms, 3 beds

20–25 Jul

$2,197 SGD for 5 nights

Pay $0 today

Free cancellation

Guest favourite

Cottage in Chester

Spectacular 3 Bedroom Lake House!

3 bedrooms, 3 beds

5–10 Sept

$2,665 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 44 reviews

Home in Chester Basin

High Water Mark

4 bedrooms, 5 beds

28 Aug – 2 Sept

$2,827 SGD for 5 nights

Pay $0 today

Free cancellation

New place to stay

Guest favourite

Flat in Chester

Seapearl Studio - adorable central apartment

1 bedroom, 1 bed

30 Aug – 4 Sept

$817 SGD for 5 nights

Free cancellation

4.87 out of 5 average rating, 52 reviews

Home in Chester Basin

Highlander House

2 bedrooms, 2 queen beds

9–14 Sept

$5,088 SGD for 5 nights

Free cancellation

New place to stay

Home in Chester

Chester Suite By The Ocean

1 bedroom, 3 beds

1–6 Aug

$1,928 SGD for 5 nights

Pay $0 today

Free cancellation

4.74 out of 5 average rating, 170 reviews

Top guest favourite

Home in Chester Basin

The Oasis on Blueberry Lane

4 bedrooms, 5 beds

7–12 Sept

$3,166 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 173 reviews

Guest favourite

Home in Chester

Witmere

4 bedrooms, 5 beds

5–10 Sept

$5,153 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Top guest favourite

Home in Chester

Beautiful home in picturesque Chester NS

4 bedrooms, 5 beds

29 Aug – 3 Sept

$3,069 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Cottage in Chester

Spacious Lakefront Cottage Retreat

3 bedrooms, 5 beds

27 Aug – 1 Sept

$1,160 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 195 reviews