Shelter Island Homes with Free Cancellation

Award-winning homes from £98

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Shelter Island

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.

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.

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.


We selected the top 3% holiday homes in Shelter Island Free Cancellation

Explore the 644 most perfect homes in our collection

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Most popular homes in Shelter Island

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

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Check upcoming rates & availability for Shelter Island Free Cancellation


Frequently asked questions

Explore our selection of the finest homes in Shelter Island with free cancellation for your peace of mind. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Our friendly team of Plum Experts are on-hand 24/7 to help you book a short or extended stay with free cancellation options in the best rentals that Shelter Island has to offer.

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