Viewing 40 of 624 rentals in Helmsley
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Vacation homes - vacation rentals
18 Vacation rentals
from $162 / night
$552 - $1,725 / week
from $288 / night
$1,219 / week
from $280 / night
$968 - $4,095 / week
from $107 / night
$430 - $1,289 / week
from $255 / night
$818 - $3,002 / week
from $165 / night
$493 - $1,433 / week
from $203 / night
$691 - $2,236 / week
from $428 / night
$2,994 / week
from $148 / night
$576 - $1,695 / week
from $229 / night
$1,603 / week
from $507 / night
$3,544 / week
from $511 / night
$3,574 / week
from $134 / night
$400 - $1,157 / week
from $243 / night
$727 - $2,309 / week
from $110 / night
$374 - $1,044 / week
from $231 / night
$805 - $2,058 / week
from $129 / night
$766 - $3,540 / week
Great rentals within 20 miles that match your search
from $412 / night
$2,884 / week
from $168 / night
$1,176 / week
from $115 / night
$804 / week
from $145 / night
$1,015 / week
from $214 / night
$1,498 / week
from $659 / night
$4,612 / week
from $263 / night
$1,839 / week
from $305 / night
$2,131 / week
from $214 / night
$1,498 / week
from $642 / night
$4,492 / week
from $572 / night
$3,999 / week
from $177 / night
$1,236 / week
from $691 / night
$4,833 / week
from $343 / night
$2,402 / week
from $249 / night
$1,062 / week
from $92 / night
$643 / week
from $165 / night
$998 / week
from $559 / night
$3,909 / week
from $99 / night
$694 / week