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Search results; 573 homes in Chestertown
573 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
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
$2,378 SGD
$1,423 SGD
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for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 240 reviews
5.0 (240)
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
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 80 reviews
4.98 (80)
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
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for 5 nights
$2,111 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 65 reviews
4.95 (65)
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
$1,505 SGD
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for 5 nights
$1,505 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
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
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 179 reviews
4.98 (179)
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, 85 reviews
4.93 (85)
Top guest favourite
Guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$842 SGD
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for 5 nights
$842 SGD for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 132 reviews
4.99 (132)
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
$822 SGD
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for 5 nights
$822 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 279 reviews
4.97 (279)
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
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for 5 nights
$2,539 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 137 reviews
4.96 (137)
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, 34 reviews
4.91 (34)
Guest favourite
Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$3,633 SGD
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for 5 nights
$3,633 SGD for 5 nights
Pay $0 today
Free cancellation
4.91 out of 5 average rating, 64 reviews
4.91 (64)
Top guest favourite
Guest favourite
Home in Worton
Cozy Cape Cod in worton MD
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
3 bathrooms
3 bathrooms
5–10 Jul
5–10 Jul
$1,687 SGD
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for 5 nights
$1,687 SGD for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
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
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 145 reviews
5.0 (145)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$949 SGD
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for 5 nights
$949 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 197 reviews
4.98 (197)
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
$1,902 SGD
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for 5 nights
$1,902 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,119 SGD
Show price breakdown
for 5 nights
$2,119 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 140 reviews
4.98 (140)
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