Shelter Island Three Bedroom Homes

We selected the 370 homes worth renting in this location

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Home spotlights in Shelter Island

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

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.

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

An idyllic escape for all the family, this waterfront home sits in the hamlet of North Sea, part of larger Southhampton, and within an easy drive of a wide selection of restaurants, boutique shops and beautiful beaches. Whether you're here for a weekend or a longer stay, you'll immediately feel relaxed in this quiet spot, surrounded by nature.


We selected the top 3% holiday homes in Shelter Island Three Bedroom Homes

Explore the 370 most perfect homes in our collection

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Most popular homes in Shelter Island

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

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Check upcoming rates & availability for Shelter Island Three Bedroom Homes


Frequently asked questions

Spacious 3 bedroom homes 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 3 bedroom homes 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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