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20 Vacation rentals

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Highland ski home to rent.

Highland house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

from $1,638 / night

$11,466 / week

1 / 30

Highland Vacation home rental

Highland house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from $432 / night

$3,024 / week

1 / 30

Ski home to rent in Highland

Highland house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $498 / night

$3,486 / week

1 / 30

Highland ski home to rent.

Highland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Pricing unknown

1 / 13

Vacation apartment in Highland

Highland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from $183 / night

$1,281 / week

1 / 15

Vacation apartment accommodation

Highland apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $120 / night

$840 / week

1 / 12

Home rental in Highland

Highland house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $616 / night

$4,312 / week

1 / 30

Home rental in Highland

Highland house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $244 / night

$1,708 / week

1 / 30

Vacation home in Highland

Highland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $833 / night

$5,831 / week

1 / 30

Highland Vacation home rental

Highland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $263 / night

$1,841 / week

1 / 30

Highland Vacation home rental

Highland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $253 / night

$1,771 / week

1 / 30

Highland Vacation home rental

Highland house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $526 / night

$3,682 / week

1 / 19

Vacation home in Highland

Highland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $565 / night

$3,955 / week

1 / 28

Home accommodation in Highland

Highland house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $942 / night

$6,594 / week

1 / 30

Vacation home in Highland

Highland house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,455 / night

$10,185 / week

1 / 30

Highland Vacation villa rental

Highland villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

from $924 / night

$6,468 / week

1 / 30

Vacation home in Highland

Highland house

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 37

from $2,769 / night

$19,383 / week

1 / 30

Vacation home in Highland

Highland house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

from $461 / night

$3,227 / week

1 / 30

Highland Vacation home rental

Highland house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $396 / night

$2,772 / week

1 / 30

Highland Vacation home rental

Highland house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $349 / night

$2,443 / week

1 / 30

Great rentals within 20 miles that match your search

Tillson Vacation home rental

Tillson house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $192 / night

$1,344 / week

1 / 21

Wallkill ski home to rent.

Wallkill house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from $354 / night

$2,478 / week

1 / 30

Newburgh Vacation home rental

Newburgh house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 2

from $1,306 / night

$9,142 / week

1 / 30

Vacation cottage in Marlboro

Marlboro cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $175 / night

$1,225 / week

1 / 21

Wallkill ski home to rent.

Wallkill house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from $563 / night

$3,941 / week

1 / 30

Villa rental in New Paltz

New Paltz villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from $828 / night

$5,796 / week

1 / 21

Ski home to rent in Beacon

Beacon house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $568 / night

$3,976 / week

1 / 30

Vacation villa in Clintondale

Clintondale villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $613 / night

$4,291 / week

1 / 21

Rhinebeck ski apartment to rent.

Rhinebeck apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $173 / night

$1,211 / week

1 / 7

Vacation home accommodation

Wappingers Falls house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 10

from $175 / night

$1,225 / week

1 / 11

Kerhonkson ski home to rent.

Kerhonkson house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $725 / night

$5,075 / week

1 / 30

Vacation villa in Hyde Park

Hyde Park villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

from $1,384 / night

$9,688 / week

1 / 30

Vacation home in Poughkeepsie

Poughkeepsie house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 3

Pricing unknown

1 / 12

Vacation apartment in Tillson

Tillson apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $186 / night

$1,302 / week

1 / 28

Vacation apartment in Pleasant Valley

Pleasant Valley apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $123 / night

$861 / week

1 / 13

Ski cottage to rent in Pleasant Valley

Pleasant Valley cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $134 / night

$938 / week

1 / 30

Vacation home in New Paltz

New Paltz house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

from $985 / night

$6,895 / week

1 / 28

Home accommodation in Wallkill

Wallkill house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $353 / night

$2,471 / week

1 / 30

Ski home to rent in Clinton Corners

Clinton Corners house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,119 / night

$7,833 / week

1 / 30

Vacation home in Dover Plains

Dover Plains house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $190 / night

$1,330 / week

1 / 15