Shelter Island Accommodation with Airport Transfers

We selected the 914 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

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Pets

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Home spotlights in Shelter Island

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls.

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.


We selected the top 3% holiday homes in Shelter Island Accommodation with Airport Transfers

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

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Frequently asked questions

Are you looking for accommodation with airport transfers in Shelter Island? You've come to the right place: chat to one of our friendly experts who can arrange for airport transfers as an addition to your booking in Shelter Island. Browse our selection of homes that come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included, and reach out to our friendly 24/7 support team if you need anything.

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