Rent Boutique Hotel Alternatives in Shelter Island

We selected the 920 homes worth renting in this location

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Home spotlights in Shelter Island

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 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, and John Steinbeck.

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.

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.

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.


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

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

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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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