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Search results; Over 1,000 homes in Chester
Over 1,000 homes in Chester
Top guest favourite
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms
,
·
4 beds
,
·
2 private bathrooms
20–25 Oct
20–25 Oct
$2,054 SGD
$1,820 SGD
Show price breakdown
for 5 nights
,
·
4.98 out of 5 average rating, 46 reviews
4.98 (46)
Top guest favourite
Guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
17–22 Oct
17–22 Oct
$1,241 SGD
$888 SGD
Show price breakdown
for 5 nights
Free cancellation
4.96 out of 5 average rating, 301 reviews
4.96 (301)
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms
4 bedrooms
,
·
4 king beds
4 king beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Sept
13–18 Sept
$3,436 SGD
Show price breakdown
for 5 nights
$3,436 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Chester
The Fitz Inn
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,310 SGD
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for 5 nights
$1,310 SGD for 5 nights
4.96 out of 5 average rating, 82 reviews
4.96 (82)
Guest favourite
Guest favourite
Home in Chester
Crab Alley: Bayfront Home + Hot Tub & Game Room
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$3,675 SGD
Show price breakdown
for 5 nights
$3,675 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 29 reviews
4.9 (29)
Featured hotel
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$692 SGD
Show price breakdown
for 5 nights
$692 SGD for 5 nights
+$103 SGD Airbnb credit
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Room in Queenstown
The Logan
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
5–10 Sept
5–10 Sept
$1,312 SGD
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for 5 nights
$1,312 SGD for 5 nights
4.91 out of 5 average rating, 53 reviews
4.91 (53)
Top guest favourite
Guest favourite
Guest suite in Grasonville
Heron's Haven
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$886 SGD
$759 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 139 reviews
5.0 (139)
Top guest favourite
Guest favourite
Flat in Grasonville
Halcyon house. Lovely views on MD eastern shore.
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$1,712 SGD
Show price breakdown
for 5 nights
$1,712 SGD for 5 nights
4.91 out of 5 average rating, 235 reviews
4.91 (235)
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
6–11 Sept
6–11 Sept
$6,025 SGD
$5,315 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Superhost
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$1,742 SGD
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for 5 nights
$1,742 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$2,087 SGD
$1,826 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 81 reviews
4.98 (81)
Guest favourite
Guest favourite
Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,881 SGD
$1,646 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 158 reviews
4.96 (158)
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
8–13 Sept
8–13 Sept
$3,215 SGD
Show price breakdown
for 5 nights
$3,215 SGD for 5 nights
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
6–11 Sept
6–11 Sept
$2,135 SGD
$1,439 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Superhost
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
13–18 Sept
13–18 Sept
$2,365 SGD
Show price breakdown
for 5 nights
$2,365 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
13–18 Sept
13–18 Sept
$3,548 SGD
Show price breakdown
for 5 nights
$3,548 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 310 reviews
4.95 (310)
Top guest favourite
Guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
2–7 Nov
2–7 Nov
$609 SGD
Show price breakdown
for 5 nights
$609 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 430 reviews
4.96 (430)
Top guest favourite
Guest favourite
Flat in Stevensville
Boutique by the Bay
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,559 SGD
$1,374 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 312 reviews
4.97 (312)
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