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Search results; 587 homes in Chestertown
587 homes in Chestertown
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom
,
·
2 beds
,
·
1 private bathroom
10–15 Aug
10–15 Aug
$948 SGD
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for 5 nights
$948 SGD for 5 nights
,
·
4.98 out of 5 average rating, 197 reviews
4.98 (197)
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
$808 SGD
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for 5 nights
$808 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 279 reviews
4.97 (279)
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
$1,274 SGD
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for 5 nights
$1,274 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
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
$2,287 SGD
$1,373 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
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
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 132 reviews
4.99 (132)
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
13–18 Oct
13–18 Oct
$1,103 SGD
$1,009 SGD
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for 5 nights
Pay $0 today
Free cancellation
4.99 out of 5 average rating, 249 reviews
4.99 (249)
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
$1,537 SGD
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for 5 nights
$1,537 SGD for 5 nights
5.0 out of 5 average rating, 85 reviews
5.0 (85)
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
$1,162 SGD
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for 5 nights
$1,162 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 80 reviews
4.98 (80)
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
$3,874 SGD
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for 5 nights
$3,874 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 107 reviews
4.95 (107)
Superhost
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$773 SGD
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for 5 nights
$773 SGD for 5 nights
Pay $0 today
Free cancellation
4.86 out of 5 average rating, 192 reviews
4.86 (192)
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
$1,506 SGD
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for 5 nights
$1,506 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 65 reviews
4.95 (65)
Guest favourite
Guest favourite
Flat in Chestertown
1-br apt in downtown Chestertown (Unit 1)
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$1,990 SGD
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for 5 nights
$1,990 SGD for 5 nights
Pay $0 today
Free cancellation
4.9 out of 5 average rating, 93 reviews
4.9 (93)
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
7–12 Jul
7–12 Jul
$1,601 SGD
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for 5 nights
$1,601 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 62 reviews
4.98 (62)
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
$2,134 SGD
$1,901 SGD
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for 5 nights
Pay $0 today
Free cancellation
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
$2,453 SGD
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for 5 nights
$2,453 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
Riverfront Retreat
6 bedrooms
6 bedrooms
,
·
11 beds
11 beds
,
·
5.5 bathrooms
5.5 bathrooms
12–17 Jul
12–17 Jul
$10,167 SGD
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for 5 nights
$10,167 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favourite
Guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$965 SGD
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for 5 nights
$965 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 180 reviews
4.92 (180)
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
$1,995 SGD
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for 5 nights
$1,995 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
Room in Still Pond
Room 2 Civil War Era House
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Jul
1–6 Jul
$670 SGD
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for 5 nights
$670 SGD for 5 nights
4.87 out of 5 average rating, 60 reviews
4.87 (60)
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