Photo by Erisa Dilo

Shelter Island Heights holiday rentals

We found 391 holiday rentals — enter your dates for availability

Discover a selection of 34 homes and other holiday rentals in Shelter Island Heights that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The lively area of Shelter Island Heights awaits your stay

Come and experience Shelter Island Heights and its opera, entertainment and theatre scene. Renowned for its island views, camping and beaches, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Shelter Island Heights

Do you want to find things to do in the area? Venture out of your cosy holiday rental and experience everything that makes Shelter Island Heights a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Kontokosta Winery (2.2 mi / 3.6 km)
  • Raphael Winery (6.4 mi / 10.3 km)
  • Pindar Vineyards (6.7 mi / 10.8 km)
  • Bedell Cellars (7 mi / 11.2 km)
  • Peconic Bay Winery (7.9 mi / 12.7 km)
  • Wolffer Estates Vineyard (10.4 mi / 16.8 km)

Exploring the natural landscape of Shelter Island Heights

Travellers enjoy Shelter Island Heights for its island views and beaches. Whether you're an adventurous traveller or just want to appreciate the scenery, Shelter Island Heights is a great place to get out in nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Sunset Beach (0.9 mi / 1.4 km)
  • 67 Steps Beach (2.6 mi / 4.2 km)
  • Orient Point County Park (8 mi / 12.8 km)
  • LongHouse Reserve (10.8 mi / 17.3 km)
  • The Hamptons Beaches (11.3 mi / 18.2 km)
  • Georgica Beach (12.7 mi / 20.4 km)

Seasonal weather averages in Shelter Island Heights

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 21°C.

Transport to and around Shelter Island Heights

The nearest airport is in East Hampton, NY (HTO), located 10.2 mi (16.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Shelter Island Heights?
According to our research, houses are considered the most popular holiday property type in Shelter Island Heights. But as you might expect, everyone’s idea of an awesome trip is bound to be different. Stayz has holiday homes in a variety of sizes and shapes, so you’re sure to find the perfect fit for you.
How much does it cost to rent a holiday home in Shelter Island Heights?
Season, length of stay and property type are some things that can influence the price of a holiday home. Simply add your travel dates to find your ideal escape. From quaint country cottages to sprawling luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Shelter Island Heights?
The average price for a holiday home near the beach in Shelter Island Heights will depend on when you’re going and the type and size of property you’re looking for. You can easily find prices on Stayz by entering your travel dates and destination. Then use our filters to select the number of bedrooms and amenities that you require, like WiFi, a pool and air conditioning.
Are there pet-friendly holiday homes in Shelter Island Heights?
Yes. There are. Take your pick of 67 holiday homes that welcome pets in Shelter Island Heights on Stayz. Our furry companions deserve a getaway too, so simply use our search function for pet-friendly holiday homes to book a property where your pooch can join the fun.
Can I rent a house with a pool in Shelter Island Heights?
Pack your swimming gear and pool noodle, because there are 41 houses with a private pool in Shelter Island Heights. Kick back at one of these sought-after holiday homes and let every day be a pool day. Simply enter your dates into Stayz, then check the “pool” filter to find a place to make a splash!
What are popular home amenities in Shelter Island Heights?
A garden, an electric car charging station and a fireplace rank as the most popular home amenities in Shelter Island Heights. Whether you’re taking to the road by yourself, with your sweetheart or a group of friends, Stayz can help you find a holiday home that suits your tastes with all the features you’ll enjoy.
Are there large group holiday homes in Shelter Island Heights?
With 16 holiday homes that can host 10 or more guests in Shelter Island Heights, there’s no need to hold back on your invites. From fun family holidays to special events like Thanksgiving or Christmas parties, Stayz will help you find a large group home to match the occasion.
Are there holiday homes in Shelter Island Heights that welcome kids?
With 66 family-friendly holiday properties to select from in Shelter Island Heights, now is a fantastic time to introduce the kids to the wonders of travel. Just click on our “Properties good for families” filter to locate stays that come with conveniences perfect for travelling families, such as full kitchens, pools, bunk beds and entertainment areas.
What are the top attractions for families in Shelter Island Heights?
Keeping the kids occupied during your holiday in Shelter Island Heights is a snap with these fabulous family-friendly attractions:

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

Are there one-bedroom holiday homes in Shelter Island Heights?
Yes, there are two one-bedroom properties in Shelter Island Heights to pick from. A one-bedroom holiday property is a wonderful option if it’s only you and your partner or if you’re flying solo. Add in more space, privacy and convenience compared to a hotel, and you’ve got yourself a memorable getaway.
Can I find two-bedroom holiday homes in Shelter Island Heights?
Choose from three two-bedroom holiday homes in Shelter Island Heights. Give the kids the second room or maybe fill it with a couple of your best buddies. There’s space for whoever’s fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Shelter Island Heights?
Whether you’d like to stay in touch with world events, check emails or surf social networks, there are 31 holiday homes with WiFi in Shelter Island Heights. Check the “WiFi” box when searching on Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Shelter Island Heights?
Work out your travel dates and then use the filters to search for holiday homes with air conditioning in Shelter Island Heights on Stayz. With 66 air-conditioned properties available here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Shelter Island Heights?
The minimum age allowed can vary across properties on Stayz, so check the rules of the holiday home in Shelter Island Heights you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a holiday home in Shelter Island Heights for?
The length of time you can rent a holiday home in Shelter Island Heights differs according to the property. Just enter your chosen dates to see a list of options offering extended stays. With tons of amenities such as air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you’re sure to discover somewhere perfect to call your home away from home in Shelter Island Heights.

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