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Search results; 373 homes in Chestertown
373 homes in Chestertown
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom
,
·
2 beds
,
·
1 private bathroom
22–27 Jul
22–27 Jul
$984 SGD
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for 5 nights
$984 SGD for 5 nights
,
·
4.98 out of 5 average rating, 197 reviews
4.98 (197)
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
$1,842 SGD
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for 5 nights
$1,842 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 241 reviews
5.0 (241)
Top guest favourite
Guest favourite
Flat in Chestertown
Secluded and romantic getaway in Chestertown
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$726 SGD
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for 5 nights
$726 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 282 reviews
4.97 (282)
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
$2,097 SGD
$1,939 SGD
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for 5 nights
Free cancellation
4.98 out of 5 average rating, 180 reviews
4.98 (180)
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
$1,505 SGD
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for 5 nights
$1,505 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 67 reviews
4.96 (67)
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
$1,810 SGD
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for 5 nights
$1,810 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 137 reviews
4.96 (137)
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
$1,312 SGD
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for 5 nights
$1,312 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 82 reviews
4.98 (82)
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
$1,996 SGD
Show price breakdown
for 5 nights
$1,996 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
$1,900 SGD
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for 5 nights
$1,900 SGD for 5 nights
4.93 out of 5 average rating, 85 reviews
4.93 (85)
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
$2,536 SGD
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for 5 nights
$2,536 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 12 reviews
5.0 (12)
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
$1,500 SGD
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for 5 nights
$1,500 SGD for 5 nights
5.0 out of 5 average rating, 95 reviews
5.0 (95)
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
$1,520 SGD
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for 5 nights
$1,520 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 63 reviews
4.98 (63)
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
$841 SGD
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for 5 nights
$841 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
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
6–11 Jul
6–11 Jul
$2,374 SGD
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for 5 nights
$2,374 SGD for 5 nights
4.91 out of 5 average rating, 35 reviews
4.91 (35)
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
$1,699 SGD
Show price breakdown
for 5 nights
$1,699 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 16 reviews
5.0 (16)
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
7–12 Jul
7–12 Jul
$2,116 SGD
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for 5 nights
$2,116 SGD for 5 nights
5.0 out of 5 average rating, 54 reviews
5.0 (54)
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
$3,628 SGD
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for 5 nights
$3,628 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 65 reviews
4.91 (65)
Top guest favourite
Guest favourite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
2.5 bathrooms
2.5 bathrooms
11–16 Jul
11–16 Jul
$2,979 SGD
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for 5 nights
$2,979 SGD for 5 nights
4.98 out of 5 average rating, 208 reviews
4.98 (208)
Top guest favourite
Guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
4 bathrooms
4 bathrooms
20–25 Sept
20–25 Sept
$4,124 SGD
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for 5 nights
$4,124 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 115 reviews
4.99 (115)
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