Shelter Island vacation rentals

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your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 87 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.

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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 for a relaxing getaway.

Activities and attractions in and around Shelter Island

Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Shelter Island has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Greenport Carousel (2.6 mi / 4.2 km)
  • Kontokosta Winery (3.5 mi / 5.7 km)
  • Raphael Winery (6.8 mi / 10.9 km)
  • Pindar Vineyards (7 mi / 11.3 km)
  • Bedell Cellars (7.3 mi / 11.7 km)
  • Peconic Bay Winery (8.1 mi / 13.1 km)

Exploring the natural features in Shelter Island

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Shelter Island is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Sunset Beach (1.5 mi / 2.4 km)
  • 67 Steps Beach (4 mi / 6.4 km)
  • Sag Harbor Marine Park (5.1 mi / 8.3 km)
  • Orient Beach State Park (5.7 mi / 9.2 km)
  • Elizabeth A. Morton National Wildlife Refuge (5.8 mi / 9.3 km)
  • Orient Point County Park (8.1 mi / 13.1 km)

How to get to and around Shelter Island

The nearest airport is in East Hampton, NY (HTO), located 8.8 mi (14.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away.

Frequently asked questions

What is the best area to stay in Shelter Island when booking a vacation rental?

Among the most sought-after areas for a Shelter Island vacation home is Dering Harbor. When you book your Vrbo vacation property, you'll have the whole place to yourself. This means you don't have to share it with anyone apart from your people.

What is the most popular type of vacation rental accommodation in Shelter Island?

According to our research, houses are the most desirable property type in Shelter Island. But having said that, everyone's idea of the perfect stay isn't going to be the same. Vrbo has vacation homes with every size, shape and budget in mind, so you're sure to find the best fit for your needs.

How much does it cost to rent a vacation rental in Shelter Island?

Length of stay, property type and time of year are among the factors that can influence the price of a vacation home. Simply add your travel dates to find your ideal escape. From cozy chalets to sprawling luxury villas, all Vrbo vacation rentals offer unbeatable value.

How much does it cost to rent a beach house in Shelter Island?

When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Enter your Shelter Island travel dates to view your options on Vrbo. Did someone just say "hot tub"? Use our filters to select the features and amenities you need.

What are popular rental amenities in Shelter Island?

A lake view, a swimming pool and nearby museums head the list of most popular rental amenities in Shelter Island. Whether you're taking to the road on your own, with a partner or a group of dear friends, Vrbo will help you find a vacation rental that suits your style with all the conveniences you're looking for.

What are the top attractions for families in Shelter Island?

Keep the kids busy at these fabulous family-friendly attractions in Shelter Island:

  • 67 Steps Beach
  • Orient Beach State Park
  • Railroad Museum of Long Island

Can I find two-bedroom vacation rentals in Shelter Island?

Gather your besties and enjoy peace, privacy and comfort in one of the five two-bedroom vacation rentals Shelter Island has to offer.

Are there vacation rentals with WiFi in Shelter Island?

Shelter Island has 27 vacation rentals with WiFi, so you can stay connected while traveling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to catching up on social media, these Vrbo homes make it easy to get online.

How old do you have to be to rent a vacation rental in Shelter Island?

The minimum required age is typically 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your preferred Shelter Island vacation home before booking.

How long can I rent a vacation rental in Shelter Island for?

The amount of time you can book a Shelter Island vacation home for depends on each property. Simply enter your travel dates to find available options that offer long-term stays. They come with all you require to make your extended vacation more convenient and comfortable, such as air conditioning and kitchens. Some vacation rentals may also offer weekly or monthly discounts, so you can have a longer stay for less.

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