Discover a selection of 445 vacation rentals in Orange County, US 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 private pools. Prices start at $125 per night, and houses and cabins are popular options for a stay in Orange County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Orange County
Destination guide

Orange County is backcountry New York

Orange County is like the stopper at the very northern end of the Great Appalachian Valley. Undulating hills where spruce firs and mountain maples shift this way and that in the breezes that drift down the Hudson River dominate the backcountry. Pretty New Yorker towns pepper its interior, from gritty Middletown to quaint Montgomery. Wineries dot the Warwick Valley, and Orange County vacation rentals lead all the way into the heart of the beautiful Catskill ranges _ think waterfalls, camping, hiking, fishing, and more.

Things to do

The famous sights of Orange County

Hone your salute and pledging of allegiances for that visit to Orange County because this cut out of New York State is home to the prestigious West Point Military Academy. Organized tours of the grounds include trips to the military cemetery and the West Point Museum _ think tales of WWII heroes, rusting tanks, and centuries-old cannons alike. And to balance that out? Well, how about some sweet tipples at the Brotherhood Winery _ said to be oldest operating winery in the entire United States?


Get out and about in Orange County

Orange County could just be the perfect place to vacation for a taste of backcountry New York State. Far away from the sprawl of the Big Apple, you're free to take to the mountain roads for scenic drives into the heart of the Catskills, or simply languish on bobbing river boats as they drift down the courses of the Hudson. Other travelers will go for something a little more adventurous, hitting the state parks and forests with camping stuff or cross-country skiing gear in tow.


Dodge the winter in Orange County

Unless you're booking those Orange County vacation rentals to rack up the cross-country skis and conquer the backcountry snow trails of the Catskills, it's certainly better to plan your trip here in the spring, summer, or fall. Each season has its own draws. April and May see the state parks come into bloom, and the weather pleasant and cool. June, July, and August are festival time, with the hottest temperatures for cruising the Hudson. And then September and October mean seeing the changing of the colors in the New York forests.

Natural features

On the doorstep of the Catskills in Orange County

Whizz down the courses of the Hudson River to see one side of Orange County, and then be sure to make a beeline for the wooded hills that dominate the district's backcountry. These are the gateway to the famous Catskill Mountains of New York State. Orange County vacation rentals there offer doorstep access to the Appalachian Trail, the powdered ski pistes of Belleayre Mountain, and cycling routes through bucolic farming communities and sylvan valleys. Meanwhile, the Kaaterskill Falls crash over the stone ridges, and white-water rapids roar down from the high peaks.

How many vacation rentals are available around Orange County, US?

Our 2021 property listings offer a large selection of 445 vacation rentals around Orange County. From 294 house rentals to 48 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Orange County?

There are many lovely places to stay for a holiday trip or just for a weekend in Orange County. From Vrbo travelers, the top most popular destinations to visit are:

  • Greenwood Lake: 135 vacation rentals
  • Fort Montgomery: 85 vacation rentals
  • Warwick: 163 vacation rentals
  • Newburgh: 572 vacation rentals
  • West Point: 214 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Orange County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Orange County?

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

  • Greenwood Lake: 135 rentals
  • Fort Montgomery: 85 rentals
  • Warwick: 163 rentals
  • Newburgh: 572 rentals
  • West Point: 214 rentals

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

Near which points of interest can I spend my holidays in Orange County?

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

  • Mount Saint Mary's College Newburgh: 255 rentals
  • Woodbury Common Premium Outlets: 229 rentals
  • Storm King Art Center: 220 rentals
  • United States Military Academy: 123 rentals
  • Warwick Valley Winery and Distillery: 197 rentals

But there are many other points of interest around Orange County listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Orange County

Greenwood Lake
135 vacation rentals
Fort Montgomery
85 vacation rentals
163 vacation rentals
572 vacation rentals
West Point
214 vacation rentals
Highland Falls
160 vacation rentals
Port Jervis
43 vacation rentals
New Windsor
117 vacation rentals
127 vacation rentals
1,001 vacation rentals
92 vacation rentals
Tuxedo Park
98 vacation rentals
159 vacation rentals
Highland Mills
104 vacation rentals
Central Valley
71 vacation rentals
53 vacation rentals
89 vacation rentals
126 vacation rentals
Sparrow Bush
73 vacation rentals
74 vacation rentals