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Search results; 527 homes in Chestertown
527 homes in Chestertown
Top guest favourite
Guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms
,
·
5 beds
,
·
4 private bathrooms
3–8 Aug
3–8 Aug
$4,207 SGD
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for 5 nights
$4,207 SGD for 5 nights
,
·
4.99 out of 5 average rating, 115 reviews
4.99 (115)
Top guest favourite
Guest favourite
Home in Chestertown
Waterfront Home with Private Dock | Peaceful Stay
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$1,538 SGD
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for 5 nights
$1,538 SGD for 5 nights
5.0 out of 5 average rating, 85 reviews
5.0 (85)
Top guest favourite
Guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
18–23 Jul
18–23 Jul
$1,275 SGD
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for 5 nights
$1,275 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 145 reviews
5.0 (145)
Top guest favourite
Guest favourite
Home in Chestertown
Gorgeous home in town center & 4 blocks from WAC
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
5–10 Jul
5–10 Jul
$2,495 SGD
$1,402 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 240 reviews
5.0 (240)
Guest favourite
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
6–11 Jul
6–11 Jul
$2,454 SGD
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for 5 nights
$2,454 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 33 reviews
4.91 (33)
Top guest favourite
Guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$1,438 SGD
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for 5 nights
$1,438 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 94 reviews
5.0 (94)
Top guest favourite
Guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
5–10 Jul
5–10 Jul
$1,507 SGD
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for 5 nights
$1,507 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 64 reviews
4.95 (64)
Top guest favourite
Guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
2.5 bathrooms
2.5 bathrooms
10–15 Jul
10–15 Jul
$1,813 SGD
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for 5 nights
$1,813 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 137 reviews
4.96 (137)
Home in Chestertown
Riverside at Pear Tree Point | Waterfront Escape
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,135 SGD
$1,949 SGD
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for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
11–16 Aug
11–16 Aug
$1,990 SGD
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for 5 nights
$1,990 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 179 reviews
4.98 (179)
Top guest favourite
Guest favourite
Flat in Chestertown
Secluded and romantic getaway in Chestertown
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
20–25 Jul
20–25 Jul
$863 SGD
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for 5 nights
$863 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 279 reviews
4.97 (279)
Top guest favourite
Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
10–15 Jul
10–15 Jul
$4,571 SGD
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for 5 nights
$4,571 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 107 reviews
4.95 (107)
Guest favourite
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$1,903 SGD
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for 5 nights
$1,903 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 84 reviews
4.93 (84)
Superhost
Superhost
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,111 SGD
Show price breakdown
for 5 nights
$2,111 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$1,163 SGD
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for 5 nights
$1,163 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 80 reviews
4.98 (80)
Superhost
Superhost
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,168 SGD
Show price breakdown
for 5 nights
$2,168 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,622 SGD
Show price breakdown
for 5 nights
$1,622 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 64 reviews
4.98 (64)
Guest favourite
Guest favourite
Room in Still Pond
Room 3 with Private Bath in Civil War Era House
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$788 SGD
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for 5 nights
$788 SGD for 5 nights
Free cancellation
4.82 out of 5 average rating, 60 reviews
4.82 (60)
Guest favourite
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1.5 bathrooms
1.5 bathrooms
6–11 Jul
6–11 Jul
$2,539 SGD
Show price breakdown
for 5 nights
$2,539 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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