Shelter Island Holiday Homes with Hot Tubs

We selected the 98 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

Riverdale

Riverdale

  • 4 guests

  • 2 bedrooms

Murray Hill, Manhattan

This home has been designed solely as a rental space, so it’s lacking in some of the warmth and character you would find in a personal home. But we were won over with the large size of the bedrooms and the sociable, open-plan communal area.

Want For Nothing

Want For Nothing

  • 11 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Nestled in East Hampton, Want For Nothing is a home that is perfectly emblematic of true Long Island glamour. Spend your time working out in the home gym and relaxing by the pool or head out for delicious brunches and walks along the seafront.

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day.

Live Love Laugh

Live Love Laugh

  • 3 guests

  • 1 bedrooms

East Harlem, Manhattan

This is a stylishly decorated apartment, located on the cusp of the Upper East Side and East Harlem. As it's a studio, it's not a large home, but it's been thoughtfully designed with some great views over the NYC cityscape.


We selected the top 3% holiday homes in Shelter Island Holiday Homes with Hot Tubs

Explore the 98 most perfect homes in our collection

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Most popular homes in Shelter Island

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

The Synagogue

The Synagogue

  • 10 guests

  • 4 bedrooms

Alphabet City, Manhattan

The Dutch Farmhouse

The Dutch Farmhouse

  • 8 guests

  • 4 bedrooms

Saugerties, New York

Rise with the Sun

Rise with the Sun

  • 20 guests

  • 8 bedrooms

Pleasant Valley, New York

The Saltwater Soul

The Saltwater Soul

  • 10 guests

  • 4 bedrooms

Mystic Islands, Little Egg Harbor Township

Dreams on the Upper East Side

Dreams on the Upper East Side

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

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Check upcoming rates & availability for Shelter Island Holiday Homes with Hot Tubs


Frequently asked questions

Discover our selection of the finest holiday homes with hot tubs for your next getaway 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 holiday homes with hot tubs 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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