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Search results283 places in Chestertown

Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Oct 15 – 20
$85 per night
Superhost
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Oct 1 – 6
$161 per night, originally $179
Home in Chestertown
Simple Living on the Pond
2 beds
Oct 1 – 6
$100 per night
Apartment in Chestertown
Loft at Fountain Park - Prime Downtown Location
5 beds
Oct 1 – 6
$299 per night
Superhost
Home in Chestertown
Cozy Victorian Downtown Home
2 beds
Oct 1 – 6
$150 per night
Superhost
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Nov 6 – 11
$119 per night
Superhost
Apartment in Chestertown
Downtown Studio Apartment
1 queen bed
Jan 6 – 13
$120 per night
Superhost
Home in Chestertown
Wren Retweet- Country Estate in Center of C’Town
6 beds
Oct 8 – 13
$178 per night, originally $248
Superhost
Apartment in Chestertown
Secluded Cottage in Middle of Chestertown
1 queen bed
Oct 22 – 27
$121 per night
Cabin in Chestertown
River Birch Cottage
4 beds
Oct 8 – 13
$206 per night
Superhost
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
3 queen beds
Oct 31 – Nov 5
$201 per night
Superhost
Home in Chestertown
Classic Victorian in Chestertown
7 beds
Oct 30 – Nov 4
$201 per night
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
2 queen beds
Oct 13 – 18
$207 per night
Room in Chestertown
Stay with Sarah And Andrew, It
Historic Private Second Floor
Oct 8 – 13
$100 per night
Superhost
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Oct 31 – Nov 5
$125 per night
Superhost
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
Oct 1 – 6
$120 per night
Superhost
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Oct 3 – 8
$165 per night
Home in Chestertown
Goose Haven, new waterfront house on Fairlee Creek
9 beds
Oct 1 – 6
$255 per night