Shelter Island Vacation Rentals with Butler Service

We selected the 920 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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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.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

An idyllic escape for all the family, this waterfront home sits in the hamlet of North Sea, part of larger Southhampton, and within an easy drive of a wide selection of restaurants, boutique shops and beautiful beaches. Whether you're here for a weekend or a longer stay, you'll immediately feel relaxed in this quiet spot, surrounded by nature.


We selected the top 3% holiday homes in Shelter Island Vacation Rentals with Butler Service

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

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Check upcoming rates & availability for Shelter Island Vacation Rentals with Butler Service


Frequently asked questions

If you're planning to book a vacation rental with butler service in Shelter Island, then look no further. Speak to one of our Plum Guide experts who can arrange for butler service to be included in your booking as an additional feature. All of our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included, so book your short or extended getaway now. Our friendly team is on hand 24/7 to offer any assistance you may need.

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