Shelter Island Homes for Four People

We selected the 528 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

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

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.

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.

A Country Call

A Country Call

  • 4 guests

  • 2 bedrooms

Bellport, Brookhaven

This sunny 1920s home lies in the heart of Bellport Village. While you'll be close to a few lovely shops and restaurants, we think you'll want a car here for getting to see the best of Long Island, not to mention the range of nearby beaches including Mother's Beach and Shirley Beach.

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.


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

Explore the 528 most perfect homes in our collection

View on map

Most popular homes in Shelter Island

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

View all

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


Frequently asked questions

Explore our collection of homes for 4 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 4 person homes that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection