Rent Boutique Hotel Alternatives in Shelter Island

We selected the 914 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Shelter Island

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.

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.

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.

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.


We selected the top 3% holiday homes in Shelter Island Boutique Hotel Alternatives

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

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Check upcoming rates & availability for Shelter Island Boutique Hotel Alternatives


Frequently asked questions

If you're on the hunt for the finest Boutique Apartment Rentals on offer in Shelter Island, then you've come to the right place. We are meticulous in our approach here at Plum Guide, accepting only the top 3% of homes in any given location, so explore our exclusive range today. Every home you see has been systematically reviewed, and comes fully furnished with all linens and essential bathroom toiletries included, as well as an expertly-equipped kitchen. Stay in one of the most remarkable Shelter Island Boutique Hotel Alternatives, and guarantee yourself a trip to remember. Don't hesitate to contact our team of experts either, because they love nothing more than helping you discover your dream home.

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