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Search results; 300 homes in Chestertown
300 homes in Chestertown
Top guest favourite
Guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio
,
·
2 beds
,
·
1 private bathroom
12–17 Jul
12–17 Jul
$785 SGD
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for 5 nights
$785 SGD for 5 nights
,
·
4.97 out of 5 average rating, 283 reviews
4.97 (283)
Top guest favourite
Guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
25–30 Aug
25–30 Aug
$2,395 SGD
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for 5 nights
$2,395 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 241 reviews
5.0 (241)
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
15–20 Aug
15–20 Aug
$1,776 SGD
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for 5 nights
$1,776 SGD for 5 nights
4.98 out of 5 average rating, 181 reviews
4.98 (181)
Top guest favourite
Guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
2–7 Aug
2–7 Aug
$1,220 SGD
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for 5 nights
$1,220 SGD for 5 nights
4.98 out of 5 average rating, 83 reviews
4.98 (83)
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
17–22 Jul
17–22 Jul
$1,640 SGD
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for 5 nights
$1,640 SGD for 5 nights
4.96 out of 5 average rating, 68 reviews
4.96 (68)
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
8–13 Jul
8–13 Jul
$1,493 SGD
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for 5 nights
$1,493 SGD for 5 nights
5.0 out of 5 average rating, 95 reviews
5.0 (95)
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
$1,808 SGD
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for 5 nights
$1,808 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 137 reviews
4.96 (137)
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
12–17 Jul
12–17 Jul
$1,965 SGD
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for 5 nights
$1,965 SGD for 5 nights
4.93 out of 5 average rating, 85 reviews
4.93 (85)
Superhost
Superhost
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$2,136 SGD
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for 5 nights
$2,136 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
10–15 Aug
10–15 Aug
$926 SGD
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for 5 nights
$926 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 133 reviews
4.99 (133)
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
8–13 Jul
8–13 Jul
$2,532 SGD
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for 5 nights
$2,532 SGD for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top 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
8–13 Jul
8–13 Jul
$2,447 SGD
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for 5 nights
$2,447 SGD for 5 nights
4.97 out of 5 average rating, 34 reviews
4.97 (34)
Top guest favourite
Guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Jul
12–17 Jul
$1,518 SGD
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for 5 nights
$1,518 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 63 reviews
4.98 (63)
Top guest favourite
Guest favourite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
11–16 Jul
11–16 Jul
$1,991 SGD
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for 5 nights
$1,991 SGD for 5 nights
5.0 out of 5 average rating, 56 reviews
5.0 (56)
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
$3,622 SGD
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for 5 nights
$3,622 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 66 reviews
4.91 (66)
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
$2,113 SGD
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for 5 nights
$2,113 SGD for 5 nights
4.98 out of 5 average rating, 141 reviews
4.98 (141)
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
23–28 Aug
23–28 Aug
$3,420 SGD
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for 5 nights
$3,420 SGD for 5 nights
4.95 out of 5 average rating, 109 reviews
4.95 (109)
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
14–19 Jul
14–19 Jul
$1,788 SGD
Show price breakdown
for 5 nights
$1,788 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Superhost
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$771 SGD
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for 5 nights
$771 SGD for 5 nights
Free cancellation
4.87 out of 5 average rating, 194 reviews
4.87 (194)
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