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Search results; 991 homes in Chester

Top guest favourite

Cottage in Chester

Moss Cottage on the Lake

1 bedroom, 1 bed, 1 private bathroom

11–16 Oct

$1,020 SGD for 5 nights

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4.95 out of 5 average rating, 152 reviews

Home in Chester

Chester Sea and Trail Getaway

3 bedrooms, 3 beds, 2 bathrooms

2–7 Aug

$2,732 SGD for 5 nights

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Free cancellation

New place to stay

Top guest favourite

Home in Chester

Endeavour Cottage

2 bedrooms, 3 beds, 2 bathrooms

4–9 Oct

$2,158 SGD for 5 nights

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Free cancellation

4.94 out of 5 average rating, 90 reviews

Guest favourite

Cottage in Chester

Spectacular 3 Bedroom Lake House!

3 bedrooms, 3 beds, 2.5 bathrooms

3–8 Oct

$2,602 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 44 reviews

Guest favourite

Guest house in Chester

The Little Caboose

1 bedroom, 1 queen bed, 1 bathroom

6–11 Sept

$1,018 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 60 reviews

Top guest favourite

Cabin in Chester

Cozy Oceanfront Escape with Hot Tub

2 bedrooms, 2 queen beds, 1 bathroom

19–24 Oct

$1,407 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 150 reviews

Top guest favourite

Cottage in Chester

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

2 bedrooms, 3 beds, 1 bathroom

15–20 Sept

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Free cancellation

4.99 out of 5 average rating, 162 reviews

Top guest favourite

Cabin in LaHave

Mid Century Aframe, Hot Tub, and Beach Access

1 bedroom, 1 queen bed, 1 bathroom

12–17 Nov

$1,752 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 485 reviews

Guest favourite

Cabin in Chester Basin

Cozy Chester cottage on the Water.

2 bedrooms, 2 beds, 1 bathroom

1–7 Sept

$1,183 SGD for 6 nights

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Free cancellation

4.9 out of 5 average rating, 31 reviews

Superhost

Home in Chester

Pine & Sea - Chester's Home for Active Families

3 bedrooms, 3 beds, 1 bathroom

21–26 Sept

$1,617 SGD for 5 nights

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Free cancellation

Top guest favourite

Home in Chester Basin

The Oasis on Blueberry Lane

4 bedrooms, 5 beds, 2.5 bathrooms

27 Sept – 2 Oct

$3,037 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 175 reviews

Top guest favourite

Home in Chester

The Whale House

3 bedrooms, 3 beds, 2 bathrooms

3–8 Sept

$2,835 SGD for 5 nights

4.99 out of 5 average rating, 70 reviews

Home in Hubbards

Cozy Coastal Retreat w/ Hot Tub | Hubbards

1 bedroom, 1 queen bed, 1 bathroom

18–23 Oct

$1,213 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Bungalow in Lunenburg

Ocean front HotTub Private Deck waterfront BBQ

1 bedroom, 1 bed, 1 bathroom

25–30 Oct

$1,452 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 292 reviews

Guest favourite

Flat in Chester

Seapearl Studio - adorable central apartment

1 bedroom, 1 bed, 1 bathroom

30 Aug – 4 Sept

$818 SGD for 5 nights

Free cancellation

4.87 out of 5 average rating, 54 reviews

Top guest favourite

Flat in Marriotts Cove

Sailors’ Paradise - Stevens Cove Guest Quarters

1 bedroom, 1 queen bed, 1 bathroom

19–24 Sept

$944 SGD for 5 nights

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Free cancellation

4.88 out of 5 average rating, 76 reviews

Home in Chester

Seaglass House

4 bedrooms, 5 beds, 2 bathrooms

7–12 Sept

$3,750 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Cottage in Chester

Spectacular 5 Bedroom Spaview Retreat!

5 bedrooms, 5 beds, 4.5 bathrooms

3–8 Oct

$4,307 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 61 reviews

Guest favourite

Home in Chester Basin

High Water Mark

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

$2,751 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 6 reviews