Shelter Island Business Accommodation

We selected the 914 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

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.

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

On the very tip of Cape Cod's curved finger, Provincetown is an East Coast beach destination like no other. Not overly developed, it's managed to retain its small-town vibe and reputation as a haven for artists and writers.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.


We selected the top 3% holiday homes in Shelter Island Business Accommodation

Explore the 914 most perfect homes in our collection

View on map

Most popular homes in Shelter Island

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Northwest Hills Planning Region

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

View all

Check upcoming rates & availability for Shelter Island Business Accommodation


Frequently asked questions

Searching for business accommodation in Shelter Island? Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. They have been tested and approved by our team of independent home critics, so you can rest assured that wifi speed or loud noises are not going to be a problem. Book today and enjoy a short or extended stay in the best business accommodation that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection