Shelter Island Homes for Five People

We selected the 372 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

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.

Sweetwater Hideaway

Sweetwater Hideaway

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Sweetwater Hideaway is a magnificently organic cabin nestled in the forestry Woodstock landscape. The timber vaulted ceiling, exposed wooden beams and deep chestnut finishings create a grand interior.

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

This characterful beach house is located in a quiet neighbourhood of Centerport, perfectly placed for you to explore Long Island. Perched on the headland, it boasts spectacular bay views.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, New York

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

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

Explore the 372 most perfect homes in our collection

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Most popular homes in Shelter Island

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Mahogany

Mahogany

  • 6 guests

  • 3 bedrooms

Amenia, Dutchess County

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

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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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