Book Dog Friendly Rental Accommodation in Shelter Island

We selected the 484 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

Soul Of The Willow

Soul Of The Willow

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock.

The Dutch Farmhouse

The Dutch Farmhouse

  • 8 guests

  • 4 bedrooms

Saugerties, New York

Set between the Hudson River and the Catskill Mountains, this spectacular 18th-century farmhouse is full of upstate New York charm. Nestled in 35 acres of secluded woodland, the house is a breath of fresh air less than two hours’ drive from the hustle and bustle of Manhattan.

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.

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.


We selected the top 3% holiday homes in Shelter Island Dog Friendly Rental Accommodation

Explore the 484 most perfect homes in our collection

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Most popular homes in Shelter Island

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Marble Muse

Marble Muse

  • 8 guests

  • 4 bedrooms

Water Mill, Southampton

High Tea & Hedgerows

High Tea & Hedgerows

  • 8 guests

  • 4 bedrooms

Pawling, New York

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

Cottontail Creek

Cottontail Creek

  • 4 guests

  • 2 bedrooms

Shandaken, New York

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Check upcoming rates & availability for Shelter Island Dog Friendly Rental Accommodation


Frequently asked questions

If you're planning a holiday and hoping to take your canine companion along for the ride, then you've certainly come to the right place. Here at Plum Guide, our collection of luxury Dog Friendly Rental Accommodation in Shelter Island consists of only the top 3% of homes. Each home is put through a vigorous vetting process, culminating in a visit from an independent Home Critic, so there is no danger of anything slipping through the cracks. Every rental in our collection comes fully furnished, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Book a stay in Dog Friendly Homes To Rent in Shelter Island now, and secure a trip to remember for all parties. To ensure the home you choose is perfect for you, seek the help of our friendly team, who are ready to assist you at any time of day.

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