Book Luxury Airbnb Alternatives in Shelter Island

We selected the 914 homes worth renting in this location

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Home spotlights in Shelter Island

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

This quintessential clapboard home in Sag Harbor is sure to pique the interest of travellers looking for a relaxing stay in the Hamptons. With its close proximity to the coast, including Haven's beach, the home is conveniently located for exploring the area.

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements.

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.

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.


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

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

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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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