Dering Harbor holiday rentals, Shelter Island: holiday houses & more

Discover a selection of holiday rentals in Dering Harbor that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a fireplace and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find the best place to stay - Dering Harbor

Orchard Manor Estate

Sleeps 15 · 6 bedrooms · 5+ bathrooms

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Condo/Apartment

Top rated rentals - Dering Harbor

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The perfect Christmas

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Enjoy full kitchens, pools, gardens and more
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Book a holiday rental for your Dering Harbor getaway

Learn about the unique charm of Dering Harbor with a stay in a holiday home rental. This city has something for everyone. 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 Dering Harbor

Do you want to find top things to see and do in the area? Venture out of your holiday home and check out everything that Dering Harbor has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Greenport Carousel (1 mi / 1.6 km)
Kontokosta Winery (1.8 mi / 2.9 km)
Raphael Winery (7.2 mi / 11.5 km)
Pindar Vineyards (7.5 mi / 12 km)
Bedell Cellars (7.7 mi / 12.4 km)
Peconic Bay Winery (8.6 mi / 13.9 km)

Exploring the natural landscape of Dering Harbor

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Dering Harbor is a great spot to appreciate mother nature. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Sunset Beach (1.6 mi / 2.6 km)
Crescent Beach (1.9 mi / 3.1 km)
67 Steps Beach (2.3 mi / 3.6 km)
Orient Beach State Park (4.9 mi / 7.9 km)
Sag Harbor Marine Park (6.9 mi / 11 km)
Orient Point County Park (7.2 mi / 11.6 km)

Transport to and around Dering Harbor

The nearest airport is in East Hampton, NY (HTO), located 10.5 mi (16.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 19.9 mi (32 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Dering Harbour?

The most in-demand types of holiday rentals in Dering Harbour are houses. Hoping for something different? Vrbo has plenty of options to match our guests' unique requirements, so you'll see holiday homes in lots of sizes and shapes. The perfect fit is ready and waiting for you — lock in yours today.

How much does it cost to rent a holiday rental in Dering Harbour?

Length of stay, season and property type are some things that can influence the price of a holiday home. Simply add your travel dates to find your perfect escape. From cosy cabins to sprawling luxury villas, all Vrbo holiday rentals offer unbeatable value.

How much does it cost to rent a beach house in Dering Harbour?

When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Enter your Dering Harbour travel dates to view your options on Vrbo. Did someone just say "hot tub"? Use the filters to choose the amenities and features you want in your beach house.

What are popular rental amenities in Dering Harbour?

Some of the most popular rental amenities people prefer in Dering Harbour include a barbecue grill, a fireplace and a swimming pool. Whether you're holidaying with friends, family or even pets, Vrbo holiday properties provide the best amenities for hanging out with the people closest to you.

What are the top attractions for families in Dering Harbour?

Keep the kids entertained at these awesome family-friendly attractions in Dering Harbour:

Shell Beach
Menhadden Lane Beach
Wades Beach

How old do you have to be to rent a holiday rental in Dering Harbour?

You should check with the Dering Harbour holiday property you're considering on Vrbo as age restrictions vary. However, typically it's 16, 18 or 21.

How long can I rent a holiday rental in Dering Harbour for?

It really depends on the Dering Harbour property. To view all available options offering extended stays, simply type your travel dates and guest number into the Vrbo search page. You can enjoy having the property to yourself, as well as amenities such as a fully-equipped kitchen and a yard where your little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.