Viewing 40 of 148 rentals in Chestertown
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Vacation homes - vacation rentals
23 Vacation rentals
from $172 / night
$1,145 / week
from $100 / night
$700 / week
from $165 / night
$1,155 / week
from $282 / night
$1,974 / week
from $125 / night
$875 / week
from $221 / night
$1,547 / week
from $401 / night
$2,807 / week
from $140 / night
$980 / week
from $170 / night
$1,190 / week
from $275 / night
$1,925 / week
from $140 / night
$980 / week
from $165 / night
$1,155 / week
from $285 / night
$1,995 / week
from $217 / night
$1,519 / week
from $170 / night
$1,190 / week
from $140 / night
$980 / week
from $51 / night
$357 / week
from $137 / night
$959 / week
from $190 / night
$1,330 / week
from $51 / night
$357 / week
from $180 / night
$1,260 / week
from $595 / night
$4,165 / week
from $125 / night
$875 / week
Great rentals within 20 miles that match your search
from $352 / night
$2,462 - $3,355 / week
from $344 / night
$2,405 - $3,848 / week
from $320 / night
$2,176 - $2,909 / week
from $344 / night
$2,405 - $3,184 / week
from $336 / night
$2,348 - $3,252 / week
from $401 / night
$2,806 - $3,481 / week
from $229 / night
$1,518 - $1,832 / week
from $344 / night
$2,405 - $3,642 / week
from $344 / night
$2,405 - $3,642 / week
from $344 / night
$2,290 - $3,413 / week
from $498 / night
$3,321 - $4,214 / week
from $58 / night
$401 / week
from $401 / night
$2,806 / week
from $825 / night
$5,775 / week
from $303 / night
$2,121 / week
from $715 / night
$5,005 / week
from $408 / night
$2,856 / week