Shelter Island Homes with Air Conditioning

We selected the 908 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Shelter Island

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.


We selected the top 3% holiday homes in Shelter Island Homes with Air Conditioning

Explore the 908 most perfect homes in our collection

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Most popular homes in Shelter Island

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

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Check upcoming rates & availability for Shelter Island Homes with Air Conditioning


Frequently asked questions

Planning to visit Shelter Island in the summer? Then the only way to guarantee a comfortable stay is to book an air conditioned home. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. The summer is a popular time of the year to visit this area, and after a day out exploring, you can properly relax and unwind in your air conditioned serviced apartment in Shelter Island.

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