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Best Hamptons House rentals on Holiday Lettings - Apartments

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156 Vacation rentals

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Home rental in Westhampton Beach

Westhampton Beach house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 18

from $2,000 / night

$14,000 / week

1 / 45

Vacation home in Westhampton Beach

Westhampton Beach house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

from $1,500 / night

$2,000 / week

1 / 50

Vacation home in Water Mill

Water Mill house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $779 / night

$5,725 / week

1 / 10

Vacation villa in Southampton

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from $2,290 / night

$13,740 / week

1 / 11

Vacation home rental

Remsenburg house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $572 / night

$4,000 / week

1 / 17

Home rental in Riverhead

Riverhead house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $298 / night

$2,086 / week

1 / 47

Vacation home rental

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from $1,031 / night

$7,214 / week

1 / 40

Vacation home rental

Montauk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $730 / night

$5,110 / week

1 / 27

East Hampton ski home to rent.

East Hampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

from $1,361 / night

$9,527 / week

1 / 30

Ski home to rent in Montauk

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $713 / night

$4,991 / week

1 / 30

Montauk Vacation home rental

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,000 / night

$7,000 / week

1 / 25

Vacation home in Montauk

Montauk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $650 / night

$4,550 / week

1 / 25

Vacation home rental

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $929 / night

$6,503 / week

1 / 22

Vacation home in East Hampton

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $789 / night

$5,523 / week

1 / 30

Sag Harbor Vacation home rental

Sag Harbor house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 13

from $1,717 / night

$12,019 / week

1 / 30

Westhampton Beach Vacation home rental

Westhampton Beach house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $1,560 / night

$10,920 / week

1 / 30

Vacation home in Hampton Bays

Hampton Bays house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $862 / night

$6,034 / week

1 / 21

East Hampton ski home to rent.

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,300 / night

$16,100 / week

1 / 30

Vacation cottage rental

Montauk cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $486 / night

$3,402 / week

1 / 16

East Hampton Vacation home rental

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $525 / night

$3,675 / week

1 / 30

Vacation home in Water Mill

Water Mill house

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 16

from $1,400 / night

$9,800 / week

1 / 30

Ski home to rent in Hampton Bays

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

from $1,021 / night

$7,147 / week

1 / 30

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $300 / night

$2,100 / week

1 / 21

Vacation home in Hampton Bays

Hampton Bays house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $989 / night

$6,923 / week

1 / 29

Vacation home in Water Mill

Water Mill house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,950 / night

$13,650 / week

1 / 30

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $510 / night

$3,570 / week

1 / 30

Ski home to rent in Hampton Bays

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 22

from $993 / night

$6,951 / week

1 / 30

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $799 / night

$5,593 / week

1 / 22

Ski home to rent in East Hampton

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $921 / night

$6,447 / week

1 / 30

Vacation home in East Hampton

East Hampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $756 / night

$5,292 / week

1 / 30

East Hampton Vacation home rental

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,686 / night

$11,802 / week

1 / 25

East Hampton Vacation home rental

East Hampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $648 / night

$4,536 / week

1 / 27

Vacation cottage in Westhampton Beach

Westhampton Beach cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $779 / night

$5,453 / week

1 / 30

Vacation home in Montauk

Montauk house

  • 1 bedroom
  • 5 bathrooms
  • sleeps 12

from $2,100 / night

$14,700 / week

1 / 30

Ski cottage to rent in Riverhead

Riverhead cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $369 / night

$2,583 / week

1 / 30

Riverhead ski cottage to rent.

Riverhead cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $452 / night

$3,164 / week

1 / 30

Ski home to rent in Sag Harbor

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $1,601 / night

$11,207 / week

1 / 26

Vacation home in Sag Harbor

Sag Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $1,999 / night

$13,993 / week

1 / 30

Westhampton Beach Vacation home rental

Westhampton Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

from $900 / night

$6,300 / week

1 / 22

Ski home to rent in Sag Harbor

Sag Harbor house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,607 / night

$11,249 / week

1 / 24

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