Book Luxury Airbnb Alternatives in Shelter Island

We selected the 936 homes worth renting in this location

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Home spotlights in Shelter Island

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Sitting alongside an enchanting creek, this cabin is a tranquil haven with a lot to offer. From the hot tub and wood fired sauna to the beautiful views, this is the perfect setting for a refreshing and romantic retreat.

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.

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 Airbnb Alternatives

Explore the 936 most perfect homes in our collection

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Most popular homes in Shelter Island

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Shelter Island to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Shelter Island Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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