Shelter Island Bed and Breakfast Alternatives

We selected the 910 homes worth renting in this location

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Home spotlights in Shelter Island

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

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.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.


We selected the top 3% holiday homes in Shelter Island Bed and Breakfast Alternatives

Explore the 910 most perfect homes in our collection

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Most popular homes in Shelter Island

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

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Check upcoming rates & availability for Shelter Island Bed and Breakfast Alternatives


Frequently asked questions

Looking for bed and breakfast style accommodation in Shelter Island? Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best bed and breakfasts that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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