Book Luxury Holiday Rentals in Shelter Island

Award-winning homes from £98

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Adults

Age 13+

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Children

Age 1 to 12

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Home spotlights in Shelter Island

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

This calming home-from-home is close enough to nip into the city on the subway, yet sits in a quiet and friendly neighbourhood in Astoria, Queens. Surrounded by leafy green parks, independent coffee shops, and a host of world cuisine eateries, it's the perfect spot for those looking to see the sights of NYC with a comforting place to call home outside of the concrete jungle.

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.


We selected the top 3% holiday homes in Shelter Island Holiday Rentals

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Shelter Island. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Shelter Island has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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