Viewing 40 of 151 rentals in Chestertown
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Vacation homes - vacation rentals
34 Vacation rentals
from $138 / night
$630 / week
from $413 / night
$2,886 - $4,312 / week
from $258 / night
$1,832 / week
from $365 / night
$2,555 / week
from $281 / night
$1,967 / week
from $268 / night
$1,876 / week
from $98 / night
$686 / week
from $125 / night
$875 / week
from $283 / night
$1,981 / week
from $399 / night
$2,793 / week
from $643 / night
$4,501 / week
from $243 / night
$1,701 / week
from $342 / night
$2,394 / week
from $834 / night
$5,838 / week
from $500 / night
$3,500 / week
from $235 / night
$1,645 / week
from $739 / night
$5,173 / week
from $145 / night
$1,015 / week
from $800 / night
$5,600 / week
from $692 / night
$4,844 / week
from $281 / night
$1,967 / week
from $1,160 / night
$8,120 / week
from $296 / night
$2,072 / week
from $638 / night
$4,466 / week
from $1,200 / night
$8,400 / week
from $575 / night
$4,025 / week
from $2,300 / night
$16,100 / week
from $526 / night
$3,682 / week
from $172 / night
$1,204 / week
from $550 / night
$3,850 / week
from $143 / night
$1,001 / week
from $167 / night
$1,169 / week
from $650 / night
$4,550 / week
from $400 / night
$2,800 / week
Great rentals within 20 miles that match your search
from $275 / night
$1,764 / week
from $228 / night
$1,595 / week
from $274 / night
$1,916 / week
from $458 / night
$2,863 - $4,787 / week
from $400 / night
$2,795 / week
from $189 / night
$1,125 / week