Shelter Island Homes for Five People

We selected the 374 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Shelter Island

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.

Venus In Furs

Venus In Furs

  • 6 guests

  • 3 bedrooms

Hudson, Columbia County

A grand townhouse in the middle of Hudson, Venus In Furs is not only a great place for exploring the Catskills and the Hudson Valley, but it’s also a destination in its own right. Whether sinking into the plush Chesterfield, or spending long evenings around the fire pit, you have plenty of options when it comes to relaxation.

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

Make the most of the New York state countryside from this home in Amenia, which is within driving distance of some excellent hikes, such as Macedonia Brook State Park (twenty minutes in the car). It’s also only thirty minutes from the Catamount ski resort, meaning there’s plenty on offer for active guests.

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.


We selected the top 3% holiday homes in Shelter Island Homes for Five People

Explore the 374 most perfect homes in our collection

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Most popular homes in Shelter Island

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Autumnal Colours

Autumnal Colours

  • 6 guests

  • 3 bedrooms

Greene County, Durham

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Check upcoming rates & availability for Shelter Island Homes for Five People


Frequently asked questions

Explore our collection of homes for 5 people 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 5 person 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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