Discover a selection of 2,500 vacation rentals in Orient, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $353 per night, and houses and cottages are popular options for a stay in Orient. Either way, you'll find a rental for everyone's needs.
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Destination guide

Oyster beds and fine wine in Orient

Orient sits on the promontory at the furthest end of Long Island, located on the quieter North Fork, away from the glitz (and prices) of the Hamptons. Originally named Oyster Ponds for the thriving beds, it's still a place to find top quality shellfish, organic farms and wineries. Although quiet in winter, the small town sees an influx of vacationers over the summer months. With architecture spanning 300 years, the town is a living museum to the history of New England. Your Orient vacation rental is perfect for a pristine summer getaway by the sea.

Things to do

Maritime history or a tour for the grown-ups

The East End Seaport Museum is not to be missed when staying in an Orient vacation rental. Learn all about the history of shipbuilding in Greenport, discover why the lighthouse is nicknamed "Bug" and stroll through the exhibitions on immigration to the states in the late 19th century and early 20th century. For the adults only, a vintage winetasting tour by van takes in 4 gorgeous vineyards, with a boozy farm lunch in the afternoon sunshine. There's no need to worry about driving home, as the tour will drop you straight back at your Orient vacation rental afterwards.

Activities

See Long Island from the sea

When you've had enough of sunbathing and playing in the waves, you might consider one of the many daytime cruises leaving Orient and nearby Greenport. With such an illustrious history of maritime immigration, a tour of the 9 lighthouses that guide shipping into New York, together with 2 revolutionary-era forts and the architecture of Long Island is a must. Alternatively, jump aboard America's first solar-powered boat to learn about the history of Peconic Bay and the lives of its first settlers. Relax and take in the stunning scenery as you head back to port and your Orient vacation rental.

Weather

Summer's best

Summer on Long Island is certainly the best time to visit Orient, when the high season is in full flow and there's lots to do. That said, those with more flexibility can avoid the crowds and bag themselves a great deal on an Orient vacation rental by searching outside of the school summer break. Visit the area in winter and you'll literally find the place to yourself. Most of the businesses close and even the locals leave, but if windswept sandy beaches and rough surf are your thing, you'll surely find it here, with few disturbances.

Natural features

A twitcher's delight

The Orient Beach State Park is a long, thin spit of land across the bay from Orient itself. The saltwater marshes have been designated an important bird area and attract herons, egrets and ospreys to nest and mate among the reeds. Running down the center of the park is a maritime wooded area with red cedar, black oak and prickly pear. Visitors can wander through the forest or fish and swim in the bay. A looped nature trail is popular with cyclists and joggers looking for scenic views as they exercise.

How to get there

How to get to and around Orient

The nearest airport is in East Hampton, NY (HTO), located 12.6 mi (20.3 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 15 mi (24.1 km) away.

How many vacation rentals are available around Orient, NY?

Our 2020 property listings offer a large selection of 2,268 vacation rentals around Orient. From 2,132 house rentals to 165 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Orient?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Orient:

  • Westbrook Center: 55 vacation rentals
  • Saybrook Manor: 34 vacation rentals
  • Madison Center: 29 vacation rentals
  • Old Saybrook Center: 16 vacation rentals
  • East Hampton North: 284 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Orient?

Vrbo offers a large selection of vacation rentals near lovely places in Orient. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Orient Beach State Park: 2,682 vacation rentals
  • Orient Point County Park: 2,541 vacation rentals
  • Orient By The Sea Marina: 2,549 vacation rentals
  • Oysterponds Historical Society: 2,513 vacation rentals
  • Island's End Golf & Country Club: 2,405 vacation rentals

But there are many other points of interest around Orient listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Orient?

Yes, of course. Vrbo has 2,132 Houses in Orient. Our other popular types of vacation rentals in Orient include:

  • Cottages: 165 rentals available
  • Cabins: 165 rentals available
  • Condos/Apartments: 53 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Orient?

Yes, you can select your preferred vacation rental with pool among our 1,424 vacation rentals with pool available in Orient. Please use our search bar to access the selection of vacation rentals available.

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