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Over 1,000 places in Chestertown

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Includes all fees, before taxes
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Jun 5 – 10
$158 per night, originally $176
Apartment in Chestertown
Secluded Cottage in Middle of Chestertown
2 queen beds
Jul 28 – Aug 2
$137 per night
Superhost
Room in Chestertown
Stay with Sarah, It
Historic Private Second Floor
Jun 5 – 10
$100 per night
4
Reviews
5.0
Rating
Home in Chestertown
All New Luxury Historical Brick Victorian Downtown
2 beds
Jun 11 – 16
$299 per night
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
Jun 25 – Jul 1
$201 per night
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
Jul 24 – 29
$191 per night
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Jul 20 – 27
$81 per night, originally $101
Superhost
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Jul 5 – 11
$158 per night
Superhost
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
Jun 25 – 30
$120 per night
Superhost
Farm stay in Chestertown
Outrange at Blue Heron Farm
2 beds
Jun 11 – 16
$210 per night
Superhost
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
Jul 1 – 6
$156 per night, originally $178
Superhost
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Jul 11 – 16
$147 per night
Superhost
Apartment in Chestertown
Downtown Studio Apartment
2 queen beds
Oct 29 – Nov 4
$174 per night, originally $228
Superhost
Home in Chestertown
Wren Retweet- Country Estate in Center of C’Town
5 beds
Aug 6 – 11
$241 per night
Superhost
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Jun 25 – 30
$119 per night
Superhost
Home in Chestertown
Historic downtown Chestertown Home. #1 Location.
3 beds
Jun 5 – 10
$260 per night
Superhost
Home in Chestertown
Duchess of Kent: Walk to downtown & College
8 beds
Jun 12 – 17
$420 per night
Superhost
Home in Chestertown
renovated place w/ cedar siding
3 beds
Jun 11 – 18
$131 per night, originally $164
Superhost