Book Luxury Vacation Rentals with a Private Chef in Shelter Island

We selected the 914 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Shelter Island

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 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, Nora Ephron and John Steinbeck.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

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


We selected the top 3% holiday homes in Shelter Island Vacation Rentals with a Private Chef

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

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Frequently asked questions

Explore our unbeatable collection of luxury Vacation Rentals with a Personal Chef in Shelter Island. Each and every home in our range comes fully furnished with excellently-equipped kitchens, essential bathroom toiletries, and all necessary linens included. Tested aspects of any home range from Wifi speed and shower pressure to a space's feel and design, so there really is nothing left to chance on our mission to discover the greatest properties on offer. Enjoy a stay in one of the Holiday Rentals in Shelter Island with a Private Chef today, and remember your trip for all the right reasons. And don't hesitate to contact our team of experts if you require any assistance, as it is their pleasure to help make the process easy.

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