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Areas near Shelter Island

Travelers going to Shelter Island are booking August dates now. Secure your vacation rental today and have the perfect trip.

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The Farmhouse

  • 5
  • 14
  • Min stay varies

$596

Details

1 / 13

New North Fork Beach Condo, Pool, Resort, Heart of the Wineries

  • 2
  • 6
  • 2 nights min

$307

Details

1 / 23

NEW! 1BR Greenport Apartment - Recently Remodeled!

  • 1
  • 2
  • Min stay varies

$186

Details

1 / 28

Elegant Designer Hamptons Retreat in Sag Harbor

  • 5
  • 12
  • Min stay varies

$2143

Details

1 / 25

The Captain's House

  • 3
  • 8
  • Min stay varies

$224

Details

1 / 26

Sunshine Bungalow Shelter Island Retreat

  • 2
  • 6
  • Min stay varies

$397

Details

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NEW! 2BR Greenport Apartment - Heart of Downtown!

  • 2
  • 4
  • Min stay varies

$283

Details

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Architect Designed Home in Waterfront Village

  • 2
  • 4
  • 6 nights min

$355

Details

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NEW! Greenport Studio Apt - Downtown Location!

  • 1
  • 2
  • Min stay varies

$171

Details

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Waterfront Charmer on idyllic Shelter Island

  • 3
  • 8
  • 14 nights min

$922

Details

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>>> ROMANTIC Beach Getaway! Seclusion, Waterfalls

  • 2
  • 6
  • Min stay varies

$392

Details

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Fabulous Beach Getaway

  • 3
  • 6
  • 7 nights min

$639

Details

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