Viewing 40 of 246 rentals in Chestertown
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Vacation homes - vacation rentals
31 Vacation rentals
from $687 / night
$4,580 - $5,382 / week
from $401 / night
$3,206 - $4,008 / week
from $175 / night
$1,225 / week
from $100 / night
$700 / week
from $350 / night
$2,450 / week
from $295 / night
$2,065 / week
from $277 / night
$1,939 / week
from $125 / night
$875 / week
from $750 / night
$5,250 / week
from $668 / night
$4,676 / week
from $149 / night
$1,043 / week
from $253 / night
$1,771 / week
from $404 / night
$2,828 / week
from $170 / night
$1,190 / week
from $942 / night
$6,594 / week
from $140 / night
$980 / week
from $238 / night
$1,666 / week
from $176 / night
$1,232 / week
from $140 / night
$980 / week
from $150 / night
$1,050 / week
from $321 / night
$2,247 / week
from $699 / night
$4,893 / week
from $331 / night
$2,317 / week
from $170 / night
$1,190 / week
from $140 / night
$980 / week
from $256 / night
$1,792 / week
from $190 / night
$1,330 / week
from $595 / night
$4,165 / week
from $180 / night
$1,260 / week
from $522 / night
$3,654 / week
from $140 / night
$980 / week
Great rentals within 20 miles that match your search
from $745 / night
$5,153 / week
from $320 / night
$2,176 - $2,909 / week
from $336 / night
$2,348 - $3,252 / 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 $916 / night
$6,412 / week
from $498 / night
$3,321 - $4,214 / week
from $401 / night
$2,806 / week