Discover a selection of 2,000 vacation rentals in Shelter Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $260 per night, and houses and cottages are popular options for a stay in Shelter Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Shelter Island
Destination guide

Welcome to the "UnHamptons" - Shelter Island

Hop on a ferry boat from the eastern shores of Long Island and you can be enjoying the relaxed vibe of Shelter Island in mere minutes. This quiet island escape is fondly known as The UnHamptons by visiting New Yorkers, who use it as a weekend retreat. Covering an area of just 4.5 square miles, a Shelter Island vacation rental makes a great base to explore the island. Rent a bike and visit the historic Sylvester Manor Educational Farm, enjoy a leisurely picnic on Shell Beach, or spot herons and ospreys at the Mashomack Nature Preserve.

Things to do

Shelter Island - a plantation nation

Aside from just feeling the sand between your toes, Shelter Island has a wealth of history. You can easily spend an hour or so exploring the historic Sylvester Manor, an educational farm and manor house which dates back to 1652. A former plantation, the manor house and grounds are open to the public for tours between Tuesday and Saturday. Now you've got a taste for island history, dig deep into Shelter Island's past at the Havens House Museum. Run by the Shelter Island Historical Society, Havens House was built in 1743 and features a fascinating array of period displays.


An island of peachy beach adventures

Shelter Island life is all about the beach, just ask any local. There are 3 main beaches on the island. Crescent Beach attracts watersports enthusiasts, who come for a cheery paddle around the island. It has a cafe, lifeguards, and several places to rent kayaks and paddleboards. The pristine sands of Shell Beach and Wades Beaches are perfect for sunbathing and beach picnics. It's also popular with the golfing crowd, who come to tee off on the island's 2 golf courses that, along with a minigolf course, will satisfy any wannabe Tiger Woods.


Summer swelters on Shelter Island

Shelter Island has been popular weekend getaway for savvy New Yorkers for decades. Although a year-round vacation destination, that's not to say the weather is great all year round. During the summer months, expect dry days with plenty of sunshine and a higher than average humidity. However, in winter, the mercury drops dramatically and snow is all but guaranteed. If you book a Shelter Island vacation rental in the shoulder seasons, spring and fall, you'll find cool but sunny days, and lots more rain, so be prepared to get soaked.

Natural features

Discover the Sound of silence at the Mashomack Preserve

Less than a 10-minute ferry ride from the eastern shores of Long Island, Shelter Island lies a 100 miles east of New York City. Surrounded by the cool clear waters of the Block Island Sound, Shelter Island hosts loads of marine life, with dolphins, and humpback and pilot whales regularly spotted from the shore. Large swathes of the island are part of the Mashomack Preserve, which has 10 miles of coastline and salt marshes. It's a big draw for the state's birdwatchers, who flock to spot osprey, great blue heron, and the snowy egret.

How to get there

Traveling to and around Shelter Island

The nearest airport is in East Hampton, NY (HTO), located 7.6 mi (12.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 20 mi (32.2 km) away.

How many vacation rentals are available around Shelter Island?

Our 2021 property listings offer a large selection of 1,852 vacation rentals around Shelter Island. From 1,768 house rentals to 99 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.