Book Luxury Airbnb Alternatives in Shelter Island

We selected the 918 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Shelter Island

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.

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.

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.


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

Explore the 918 most perfect homes in our collection

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Most popular homes in Shelter Island

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

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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