Shelter Island holiday 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 holiday rentals in Shelter Island that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
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Scenic Shelter Island will entice you

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

Activities and attractions in and around Shelter Island

Are you searching for attractions to see in the area? Venture out of your holiday home and experience everything that makes Shelter Island a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to take in the scenery, Shelter Island is a great place to spend some time outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • 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 centre. If you can't find a flight that works for your travel itinerary, you might consider flying into 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 holiday home?

Among the most sought-after areas for a Shelter Island holiday home is Dering Harbour. When you book your Vrbo holiday 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 holiday home 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 holiday 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 holiday home in Shelter Island?

Length of stay, property type and time of year are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your ideal escape. From cosy chalets to sprawling luxury villas, all Vrbo holiday homes 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 home amenities in Shelter Island?

A lake view, a swimming pool and nearby museums head the list of most popular home 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 holiday home 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 holiday homes in Shelter Island?

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

Are there holiday homes with WiFi in Shelter Island?

Shelter Island has 27 holiday homes with WiFi, so you can stay connected while travelling. 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 holiday home 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 holiday home before booking.

How long can I rent a holiday home in Shelter Island for?

The amount of time you can book a Shelter Island holiday 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 holiday more convenient and comfortable, such as air conditioning and kitchens. Some holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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