Shelter Island Homes for Four People

We selected the 524 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, New York

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 Ashokan

The Ashokan

  • 4 guests

  • 2 bedrooms

Glenford, West Hurley

The Ashokan is an exquisite barn-styled house nestled within rich woodland landscape. The quaint exterior shelters an incredibly contemporary and stylish interior.

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.


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

Explore the 524 most perfect homes in our collection

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Most popular homes in Shelter Island

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, New York

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Hearthside Haven

Hearthside Haven

  • 4 guests

  • 2 bedrooms

Ulster County, Woodstock

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

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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.

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