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Best Hamptons House rentals on Holiday Lettings - Apartments

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Great rentals within 20 miles that match your search

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Montauk ski studio to rent.

Montauk studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 filter does not match: Private fishing lake or river

from $257 / night

$1,799 / week

1 / 10

Great rentals within 20 miles that match your search

Ski cottage to rent in East Hampton

East Hampton cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $800 / night

$5,600 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Southampton

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Private fishing lake or river

from $783 / night

$5,481 / week

1 / 29

Great rentals within 20 miles that match your search

Ski cottage to rent in Sag Harbor

Sag Harbor cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Private fishing lake or river

from $457 / night

$3,199 / week

1 / 22

Great rentals within 20 miles that match your search

Ski home to rent in Amagansett

Amagansett house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Private fishing lake or river

from $1,250 / night

$8,750 / week

1 / 30

Great rentals within 20 miles that match your search

Montauk ski home to rent.

Montauk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $700 / night

$4,900 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Montauk

Montauk house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 filter does not match: Private fishing lake or river

from $1,332 / night

$9,324 / week

1 / 30

Great rentals within 20 miles that match your search

East Hampton ski home to rent.

East Hampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Private fishing lake or river

from $1,361 / night

$9,527 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Sag Harbor

Sag Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Private fishing lake or river

from $1,004 / night

$7,028 / week

1 / 23

Great rentals within 20 miles that match your search

Southampton ski home to rent.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Private fishing lake or river

from $1,745 / night

$12,215 / week

1 / 30

Great rentals within 20 miles that match your search

Amagansett ski cottage to rent.

Amagansett cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Private fishing lake or river

from $730 / night

$5,110 / week

1 / 30

Great rentals within 20 miles that match your search

Southampton ski home to rent.

Southampton house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 14

1 filter does not match: Private fishing lake or river

from $1,378 / night

$9,646 / week

1 / 30

Great rentals within 20 miles that match your search

East Hampton ski home to rent.

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $950 / night

$6,650 / week

1 / 30

Great rentals within 20 miles that match your search

Shelter Island Heights ski cottage to rent.

Shelter Island Heights cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Private fishing lake or river

from $308 / night

$2,156 / week

1 / 18

Great rentals within 20 miles that match your search

Ski home to rent in Westhampton Beach

Westhampton Beach house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Private fishing lake or river

from $1,670 / night

$11,690 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Montauk

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Private fishing lake or river

from $713 / night

$4,991 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Sag Harbor

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 filter does not match: Private fishing lake or river

from $682 / night

$4,774 / week

1 / 18

Great rentals within 20 miles that match your search

Ski home to rent in Hampton Bays

Hampton Bays house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Private fishing lake or river

from $1,500 / night

$10,500 / week

1 / 28

Great rentals within 20 miles that match your search

Water Mill ski home to rent.

Water Mill house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

1 filter does not match: Private fishing lake or river

from $707 / night

$4,949 / week

1 / 30

Great rentals within 20 miles that match your search

East Hampton ski home to rent.

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $1,748 / night

$12,236 / week

1 / 19

Great rentals within 20 miles that match your search

Ski home to rent in East Quogue

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Private fishing lake or river

from $1,495 / night

$10,465 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Private fishing lake or river

from $905 / night

$6,335 / week

1 / 28

Great rentals within 20 miles that match your search

Sag Harbor ski home to rent.

Sag Harbor house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Private fishing lake or river

from $1,184 / night

$8,288 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Southampton

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Private fishing lake or river

from $580 / night

$4,060 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in East Hampton

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $1,252 / night

$8,764 / week

1 / 28

Great rentals within 20 miles that match your search

Montauk ski home to rent.

Montauk house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Private fishing lake or river

from $521 / night

$3,647 / week

1 / 25

Great rentals within 20 miles that match your search

Hampton Bays ski home to rent.

Hampton Bays house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Private fishing lake or river

from $516 / night

$3,612 / week

1 / 21

Great rentals within 20 miles that match your search

East Hampton ski home to rent.

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Private fishing lake or river

from $395 / night

$2,765 / week

1 / 27

Great rentals within 20 miles that match your search

Southampton ski home to rent.

Southampton house

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 12

1 filter does not match: Private fishing lake or river

from $1,079 / night

$7,553 / week

1 / 24

Great rentals within 20 miles that match your search

Montauk ski condo to rent.

Montauk condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $1,400 / night

$9,800 / week

1 / 25

Great rentals within 20 miles that match your search

Hampton Bays ski home to rent.

Hampton Bays house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

1 filter does not match: Private fishing lake or river

from $1,955 / night

$13,685 / week

1 / 22

Great rentals within 20 miles that match your search

East Hampton ski home to rent.

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $1,154 / night

$8,078 / week

1 / 29

Great rentals within 20 miles that match your search

Ski home to rent in Sagaponack

Sagaponack house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $625 / night

$4,375 / week

1 / 30

Great rentals within 20 miles that match your search

Montauk ski home to rent.

Montauk house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Private fishing lake or river

from $1,500 / night

$10,500 / week

1 / 23

Great rentals within 20 miles that match your search

Ski home to rent in Montauk

Montauk house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Private fishing lake or river

from $798 / night

$5,586 / week

1 / 30

Great rentals within 20 miles that match your search

Southampton ski home to rent.

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Private fishing lake or river

from $600 / night

$4,200 / week

1 / 13

Great rentals within 20 miles that match your search

Ski home to rent in Amagansett

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Private fishing lake or river

from $611 / night

$4,277 / week

1 / 19

Great rentals within 20 miles that match your search

Ski home to rent in Remsenburg

Remsenburg house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 16

1 filter does not match: Private fishing lake or river

from $2,223 / night

$15,561 / week

1 / 30

Great rentals within 20 miles that match your search

Montauk ski condo to rent.

Montauk condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Private fishing lake or river

from $342 / night

$2,394 / week

1 / 30

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