Photo by tom owens

Shelter Island vacation rentals

We found 2,419 vacation rentals — enter your dates for availability

Discover a selection of 83 homes and other vacation rentals in Shelter Island that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the amenities you expect and more, which might include WiFi and a fireplace. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Shelter Island

Showing deals for:Aug 15 - Aug 22
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Beautiful Shelter Island will entice you

The area's history and museums are just a few of the reasons to vacation in Shelter Island. Travelers to this scenic city praise the island views, kayaking and parks. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

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.

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 to and around Shelter Island

The nearest airport is in MacArthur Airport (ISP), located 44.1 mi (70.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to East Hampton, NY (HTO), which is 8.8 mi (14.2 km) away.

Frequently asked questions

What is the best area to stay in Shelter Island when booking a vacation rental?
If you’re organizing a getaway to Shelter Island, Dering Harbor is one of the most popular locations to stay. Whether you go for a condo, cottage or another property style, you’ll always have the entire place to yourself.
What is the most popular type of vacation rental accommodation in Shelter Island?
The most in-demand types of vacation rentals in Shelter Island are cottages. Want something different? Vrbo has numerous options to match our guests’ unique needs, so you’ll see vacation properties in lots of shapes and sizes. The perfect fit is ready and waiting for you — grab yours today.
How much does it cost to rent a vacation rental in Shelter Island?
A range of things can influence how much you pay for a vacation rental in Shelter Island, including the length of stay, season and type of property. However, all of our vacation homes have one thing in common — excellent value. Simply add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Shelter Island?
The average price for a vacation rental by the beach in Shelter Island will depend on when you’ll be there and the size and type of property you want. Find prices easily and quickly on Vrbo by entering the dates you’ll be traveling. Then use the handy filters to choose the number of bedrooms and amenities that you need, like a pool, air conditioning and WiFi.
What are popular rental amenities in Shelter Island?
A water view, a sauna and a garden are the most popular rental amenities in Shelter Island. Whether you plan to travel solo, with your other half or a group of dear friends, Vrbo can help you find a vacation rental that fits your tastes with all the conveniences you’re looking for.
What are the top attractions for families in Shelter Island?
You’ll find lots of fabulous things to do and see with the family in Shelter Island, including:

  • Havens House
  • Mashomack Preserve
  • Gardiner’s Bay Country Club

Can I find two-bedroom vacation rentals in Shelter Island?
Shelter Island has nine two-bedroom vacation properties to select from. Book a vacation home with all the privacy and comfort you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Shelter Island?
Choose from 40 vacation rentals with WiFi in Shelter Island. If you want to disconnect from daily life on your vacation, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Shelter Island?
The minimum age can vary across properties on Vrbo, so be sure to check the rules of the vacation home in Shelter Island you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a vacation rental in Shelter Island for?
The length of time you can book a vacation rental in Shelter Island differs according to the property. Just enter your selected travel dates to view a list of options offering extended stays. With many features like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to discover someplace just right to call your home away from home in Shelter Island.
Does Vrbo offer discounts for vacation homes in Shelter Island?
On Vrbo, we’ve got some incredible discounts and bargains for Shelter Island. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a mini getaway or an extended stay, Vrbo offers options for every style and budget.

More Vacation Rentals ideas

People also search for