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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.

1 / 10

The Farmhouse

  • 5
  • 14
  • Min stay varies

$600

Details

1 / 8

Greenport Village Walking Distance to All

  • 2
  • 4
  • 7 nights min

$401

Details

1 / 13

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

  • 2
  • 6
  • 2 nights min

$310

Details

1 / 25

The Captain's House

  • 3
  • 8
  • Min stay varies

$226

Details

1 / 9

Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!

  • 2
  • 6
  • 2 nights min

$389

Details

1 / 14

Waterfront Condo C204 at The Cliffside Resort

  • 2
  • 6
  • 2 nights min

$300

Details

1 / 23

NEW! 1BR Greenport Apartment - Recently Remodeled!

  • 1
  • 2
  • Min stay varies

$186

Details

1 / 13

Remodeled Greenport Farmhouse

  • 3
  • 6
  • 14 nights min

$425

Details

1 / 22

Historic Greenport Walk to Town

  • 4
  • 9
  • Min stay varies

$543

Details

1 / 16

Historic Cottage Near Beach!

  • 2
  • 4
  • Min stay varies

$233

Details

1 / 19

Victorian Seasons Stirling

  • 5
  • 9
  • 1 night min

$851

Details

1 / 26

Sunshine Bungalow Shelter Island Retreat

  • 2
  • 6
  • Min stay varies

$401

Details

1 / 23

Family and Friends in Greenport

  • 4
  • 10
  • 2 nights min

$300

Details

1 / 18

Architect Designed Home in Waterfront Village

  • 2
  • 4
  • 6 nights min

$357

Details

1 / 16

Greenport Village Home Walking Distance to All

  • 3
  • 8
  • 30 nights min

$517

Details

1 / 24

NEW! 2BR Greenport Apartment - Heart of Downtown!

  • 2
  • 4
  • Min stay varies

$285

Details

1 / 22

NEW! Greenport Studio Apt - Downtown Location!

  • 1
  • 2
  • Min stay varies

$171

Details

1 / 19

Waterfront Charmer on idyllic Shelter Island

  • 3
  • 8
  • 14 nights min

$929

Details

1 / 20

>>> ROMANTIC Beach Getaway! Seclusion, Waterfalls

  • 2
  • 6
  • Min stay varies

$396

Details

1 / 25

Fabulous Beach Getaway

  • 3
  • 6
  • 7 nights min

$644

Details

1 / 47

NEW! Luxury 4BR ‘Shelter Island Hideaway’ w/ Pool!

  • 4
  • 10
  • Min stay varies

$496

Details

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