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Search results; Over 1,000 homes in Chester
Over 1,000 homes in Chester
Top guest favourite
Guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom
,
·
1 bed
,
·
1 private bathroom
26–31 Jul
26–31 Jul
$799 SGD
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for 5 nights
$799 SGD for 5 nights
,
·
4.96 out of 5 average rating, 291 reviews
4.96 (291)
Guest favourite
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
10–15 Aug
10–15 Aug
$4,923 SGD
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for 5 nights
$4,923 SGD for 5 nights
Free cancellation
4.88 out of 5 average rating, 24 reviews
4.88 (24)
Top guest favourite
Guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
17–22 Jul
17–22 Jul
$3,878 SGD
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for 5 nights
$3,878 SGD for 5 nights
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Top guest favourite
Guest favourite
Home in Chester
The Fitz Inn
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$1,326 SGD
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for 5 nights
$1,326 SGD for 5 nights
4.96 out of 5 average rating, 80 reviews
4.96 (80)
Top guest favourite
Guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
18–23 Jul
18–23 Jul
$1,982 SGD
Show price breakdown
for 5 nights
$1,982 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 112 reviews
4.91 (112)
Guest favourite
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,929 SGD
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for 5 nights
$1,929 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Superhost
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
2–7 Aug
2–7 Aug
$3,819 SGD
$3,104 SGD
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for 5 nights
4.89 out of 5 average rating, 19 reviews
4.89 (19)
Home in Chester
Farmhouse by the Sea *Pool Pass*
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
19–24 Jul
19–24 Jul
$2,878 SGD
$2,519 SGD
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for 5 nights
Top guest favourite
Guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Jul
26–31 Jul
$1,656 SGD
$1,485 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 61 reviews
5.0 (61)
Guest favourite
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
17–22 Jul
17–22 Jul
$3,083 SGD
$2,271 SGD
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for 5 nights
4.98 out of 5 average rating, 85 reviews
4.98 (85)
Top guest favourite
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$3,377 SGD
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for 5 nights
$3,377 SGD for 5 nights
Book early to save
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Top guest favourite
Guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$1,666 SGD
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for 5 nights
$1,666 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
19–24 Jul
19–24 Jul
$5,081 SGD
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for 5 nights
$5,081 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
3–8 Aug
3–8 Aug
$4,776 SGD
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for 5 nights
$4,776 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 143 reviews
4.99 (143)
Top guest favourite
Guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
26–31 Jul
26–31 Jul
$3,250 SGD
$2,841 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 50 reviews
4.98 (50)
Top guest favourite
Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
14–19 Aug
14–19 Aug
$1,733 SGD
Show price breakdown
for 5 nights
$1,733 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 463 reviews
4.97 (463)
Top guest favourite
Guest favourite
Flat in Saint Michaels
Blue Crab Lodge
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
19–24 Jul
19–24 Jul
$2,501 SGD
$2,222 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 151 reviews
4.97 (151)
Guest favourite
Guest favourite
Flat in Stevensville
Kent Island Getaway
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
17–22 Jul
17–22 Jul
$1,977 SGD
Show price breakdown
for 5 nights
$1,977 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed
1 bed
,
·
1 bathroom
1 bathroom
26–31 Jul
26–31 Jul
$929 SGD
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for 5 nights
$929 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 301 reviews
4.98 (301)
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