Discover a selection of 412 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 kitchens. Prices start at $193 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.
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 2020 property listings offer a large selection of 412 vacation rentals around Orange County. From 247 house rentals to 30 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: 114 vacation rentals
  • New Windsor: 142 vacation rentals
  • Fort Montgomery: 93 vacation rentals
  • Monroe: 118 vacation rentals
  • Highland Falls: 181 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: 114 rentals
  • New Windsor: 142 rentals
  • Fort Montgomery: 93 rentals
  • Monroe: 118 rentals
  • Highland Falls: 181 rentals

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

Can I find easy-access vacation rentals when traveling by plane to Orange County?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Orange County are:

  • Stewart International Airport (SWF): 260 vacation rentals
  • Orange County Airport (MGJ): 249 vacation rentals
  • Poughkeepsie, NY (POU-Dutchess County): 289 vacation rentals

For other airports, 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:

  • Algonquin Park: 257 rentals
  • United States Military Academy: 156 rentals
  • Orange County Genealogical Society: 252 rentals
  • Lake Tiorati Beach: 214 rentals
  • Tri-States Rock: 203 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
114 vacation rentals
New Windsor
142 vacation rentals
Fort Montgomery
93 vacation rentals
118 vacation rentals
Highland Falls
181 vacation rentals
84 vacation rentals
152 vacation rentals
546 vacation rentals
West Point
223 vacation rentals
86 vacation rentals
147 vacation rentals
913 vacation rentals
Port Jervis
39 vacation rentals
30 vacation rentals
Tuxedo Park
83 vacation rentals
Slate Hill
31 vacation rentals
Campbell Hall
65 vacation rentals
101 vacation rentals
Sparrow Bush
62 vacation rentals
56 vacation rentals