127 homes

Apartment in Chestertown
Secluded Cottage in Middle of Chestertown
1 queen bed
Oct 23 – 28
$120 per night
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Apartment in Chestertown
Downtown Studio Apartment
1 queen bed
Jan 7 – 14
$120 per night
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Guesthouse in Chestertown
Cozy Carriage House
1 bed
Oct 31 – Nov 5
$96 per night
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Farm stay in Chestertown
Outrange at Blue Heron Farm
2 beds
Dec 12 – 17
$212 per night
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Private room in Chestertown
Moonbow House #3 The Aloha Suite
1 bed
Oct 1 – 8
$51 per night
Home in Chestertown
Wren Retweet- Country Estate in Center of C’Town
5 beds
Nov 6 – 11
$175 per night, originally $200
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Nov 15 – 20
$120 per night
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Home in Chestertown
Merry Manor Pet Friendly Home
4 beds
Nov 1 – 6
$125 per night
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Apartment in Chestertown
Hillside Waterfront historic district 1BR Apt.
1 king bed
Nov 1 – 6
$157 per night
Guest suite in Chestertown
108Annex | Charming Guesthouse | Historic Downtown
1 queen bed
Oct 10 – 15
$160 per night
Cabin in Chestertown
Rivershore Retreat
3 beds
Nov 5 – 10
$297 per night
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Home in Chestertown
CHESAPEAKE SUNSETS
2 beds
Nov 7 – 14
$149 per night, originally $175
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Home in Chestertown
Lovely, Recently-Renovated Home in Chestertown
4 beds
Oct 23 – 28
$240 per night
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Private room in Chestertown
Private Bedroom and bath in Chestertown, MD
1 double bed
Oct 3 – 8
$65 per night
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Home in Chestertown
Classic Victorian in Chestertown
7 beds
Oct 31 – Nov 5
$198 per night
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Home in Chestertown
Historic house on High Street, Chestertown, MD
3 beds
Oct 14 – 19
$243 per night
Apartment in Chestertown
1-br apt in downtown Chestertown
1 queen bed
Nov 1 – 6
$136 per night
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
Oct 2 – 7
$105 per night
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Private room in Chestertown
Chestertown - Eastern Shore Getaway
3 beds
Oct 31 – Nov 5
$99 per night
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Home in Chestertown
River front cottage with private dock & water fun
11 beds
Nov 2 – 7
$450 per night
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