Discover a selection of 2,500 vacation rentals in Orient 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 kitchens. Prices start at $350 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.
AsyncDestinationUrgency
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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?

Our 2020 property listings offer a large selection of 2,458 vacation rentals around Orient. From 2,117 house rentals to 186 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Orient