Rent Luxury Accommodation for Groups in Shelter Island

We selected the 914 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Shelter Island

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.

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.

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.

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.


We selected the top 3% holiday homes in Shelter Island Accommodation for Groups

Explore the 914 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

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

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Check upcoming rates & availability for Shelter Island Accommodation for Groups


Frequently asked questions

Reserve a stay in one of the impeccable homes in our collection of luxury Group Holiday Accommodation in Shelter Island. You won't find such consistent quality anywhere else, as every single Plum Guide home comes fully furnished with all linens, a brilliantly-equipped kitchen, and essential bathroom toiletries included. Our experts really do obsess over the smallest details, with shower pressure and a bedroom's decibel levels being tested to ensure absolute quality in your hunt for the perfect home. Rent Shelter Island Accommodation for Groups today, and learn the true meaning of luxury. Call on our team of experts too, who can help you through the booking process and guarantee that you end up with the ultimate home for you.

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