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Search results; 305 homes in Chestertown
305 homes in Chestertown
Top guest favourite
Guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio
,
·
2 beds
,
·
1 private bathroom
19–24 Aug
19–24 Aug
$882 SGD
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for 5 nights
$882 SGD for 5 nights
,
·
4.97 out of 5 average rating, 289 reviews
4.97 (289)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
2–7 Nov
2–7 Nov
$979 SGD
$883 SGD
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for 5 nights
4.99 out of 5 average rating, 252 reviews
4.99 (252)
Top guest favourite
Guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms
2 bedrooms
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·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$843 SGD
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for 5 nights
$843 SGD for 5 nights
4.99 out of 5 average rating, 139 reviews
4.99 (139)
Top guest favourite
Guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$1,251 SGD
$981 SGD
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for 5 nights
4.97 out of 5 average rating, 87 reviews
4.97 (87)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$926 SGD
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for 5 nights
$926 SGD for 5 nights
4.98 out of 5 average rating, 200 reviews
4.98 (200)
Superhost
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$869 SGD
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for 5 nights
$869 SGD for 5 nights
4.87 out of 5 average rating, 195 reviews
4.87 (195)
Top guest favourite
Guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom
1 bedroom
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·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$939 SGD
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for 5 nights
$939 SGD for 5 nights
4.92 out of 5 average rating, 188 reviews
4.92 (188)
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
9–14 Aug
9–14 Aug
$1,208 SGD
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for 5 nights
$1,208 SGD for 5 nights
5.0 out of 5 average rating, 149 reviews
5.0 (149)
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
8–13 Aug
8–13 Aug
$1,515 SGD
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for 5 nights
$1,515 SGD for 5 nights
4.98 out of 5 average rating, 66 reviews
4.98 (66)
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
3–8 Aug
3–8 Aug
$1,407 SGD
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for 5 nights
$1,407 SGD for 5 nights
4.96 out of 5 average rating, 70 reviews
4.96 (70)
Top guest favourite
Guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Aug
1–6 Aug
$1,784 SGD
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for 5 nights
$1,784 SGD for 5 nights
4.98 out of 5 average rating, 124 reviews
4.98 (124)
Top guest favourite
Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms
3 bedrooms
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·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$3,709 SGD
$3,158 SGD
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for 5 nights
4.96 out of 5 average rating, 112 reviews
4.96 (112)
Top guest favourite
Guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms
2 bedrooms
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·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$1,584 SGD
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for 5 nights
$1,584 SGD for 5 nights
4.98 out of 5 average rating, 141 reviews
4.98 (141)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
17–22 Aug
17–22 Aug
$1,525 SGD
$1,373 SGD
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for 5 nights
Extended stay discount
4.97 out of 5 average rating, 101 reviews
4.97 (101)
Top guest favourite
Guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms
3 bedrooms
,
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3 queen beds
3 queen beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$1,676 SGD
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for 5 nights
$1,676 SGD for 5 nights
4.98 out of 5 average rating, 183 reviews
4.98 (183)
Guest house in Chestertown
Casa Cannon
5 bedrooms
5 bedrooms
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·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$1,012 SGD
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for 5 nights
$1,012 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Chestertown
Chesapeake Getaway | Marinas | Woodland Views
3 bedrooms
3 bedrooms
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4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Aug
1–6 Aug
$1,965 SGD
$1,337 SGD
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for 5 nights
4.88 out of 5 average rating, 33 reviews
4.88 (33)
Guest favourite
Guest favourite
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms
3 bedrooms
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4 beds
4 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$1,989 SGD
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for 5 nights
$1,989 SGD for 5 nights
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest house in Chestertown
Private 1 bedroom with access to serene backyard
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
9–14 Aug
9–14 Aug
$1,240 SGD
Show price breakdown
for 5 nights
$1,240 SGD for 5 nights
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