Shelter Island Vacation Apartments for Fashion Week

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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Home spotlights in Shelter Island

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, Southold

Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman.


We selected the top 3% holiday homes in Shelter Island Vacation Apartments for Fashion Week

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Plum guide offers a handpicked selection of the best vacation apartments in Shelter Island to stay in during fashion week. Our homes come fully furnished with the best-equipped kitchens, with luxurious interiors, and sumptuous bedrooms. Book today and enjoy a short or extended stay in the best vacation apartments in Shelter Island for fashion week. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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