Rent Boutique Hotel Alternatives in Shelter Island

We selected the 924 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Under 1

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Home spotlights in Shelter Island

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops.

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

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 Boutique Hotel Alternatives

Explore the 924 most perfect homes in our collection

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Most popular homes in Shelter Island

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

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

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

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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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