Viewing 40 of 623 rentals in Chestertown
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Vacation homes - vacation rentals
56 Vacation rentals
from $687 / night
$4,580 - $5,382 / week
from $172 / night
$1,145 / week
from $325 / night
$2,275 / week
from $356 / night
$2,492 / week
from $350 / night
$2,450 / week
from $100 / night
$700 / week
from $250 / night
$1,750 / week
from $295 / night
$2,065 / week
from $276 / night
$1,932 / week
from $282 / night
$1,974 / week
from $205 / night
$1,435 / week
from $441 / night
$3,087 / week
from $277 / night
$1,939 / week
from $449 / night
$3,143 / week
from $125 / night
$875 / week
from $290 / night
$2,030 / week
from $750 / night
$5,250 / week
from $149 / night
$1,043 / week
from $248 / night
$1,736 / week
from $365 / night
$2,555 / week
from $246 / night
$1,722 / week
from $168 / night
$1,176 / week
from $349 / night
$2,443 / week
from $404 / night
$2,828 / week
from $181 / night
$1,267 / week
from $942 / night
$6,594 / week
from $145 / night
$1,015 / week
from $250 / night
$1,750 / week
from $400 / night
$2,800 / week
from $699 / night
$4,893 / week
from $246 / night
$1,722 / week
from $109 / night
$763 / week
from $315 / night
$2,205 / week
from $51 / night
$357 / week
from $400 / night
$2,800 / week
from $253 / night
$1,771 / week
from $221 / night
$1,547 / week
from $223 / night
$1,561 / week
from $51 / night
$357 / week
from $638 / night
$4,466 / week