Viewing 40 of 175 rentals in Chestertown
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Vacation homes - vacation rentals
20 Vacation rentals
from $687 / night
$4,580 - $5,382 / week
from $401 / night
$3,206 - $4,008 / week
from $100 / night
$700 / week
from $290 / night
$2,030 / week
from $401 / night
$2,807 / week
from $248 / night
$1,736 / week
from $404 / night
$2,828 / week
from $140 / night
$980 / week
from $170 / night
$1,190 / week
from $140 / night
$980 / week
from $246 / night
$1,722 / week
from $317 / night
$2,219 / week
from $170 / night
$1,190 / week
from $140 / night
$980 / week
from $309 / night
$2,163 / week
from $230 / night
$1,610 / week
from $180 / night
$1,260 / week
from $595 / night
$4,165 / week
from $329 / night
$2,303 / week
from $119 / night
$833 / week
Great rentals within 20 miles that match your search
from $916 / night
$6,412 / week
from $745 / night
$5,153 / week
from $630 / night
$4,409 / week
from $630 / night
$4,409 / week
from $561 / night
$3,928 / week
from $825 / night
$5,775 / week
from $675 / night
$4,725 / week
from $400 / night
$2,800 / week
from $750 / night
$5,250 / week
from $900 / night
$6,300 / week
from $975 / night
$6,825 / week
from $558 / night
$3,906 / week
from $715 / night
$5,005 / week
from $375 / night
$2,625 / week
from $171 / night
$1,197 / week
from $372 / night
$2,604 / week
from $295 / night
$2,065 / week
from $410 / night
$2,870 / week
from $495 / night
$3,465 / week
from $640 / night
$4,480 / week