Shelter Island Homes for Four People

We selected the 518 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

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

This beautiful old clapboard church has been turned into a woodland retreat like no other, where deer regularly stroll among the trees. Just outside Woodstock, there are craft beer breweries, farm shops and mom and pop coffee shops a short drive away, and trails into the Catskills are all around.

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.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.


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

Explore the 518 most perfect homes in our collection

View on map

Most popular homes in Shelter Island

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

A Country Call

A Country Call

  • 4 guests

  • 2 bedrooms

Bellport, Brookhaven

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

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