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.


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.

Where to stay around Orange County?

Our 2019 property listings offer a large selection of 114 vacation rentals near Orange County. From 76 Houses to 13 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Orange County for a holiday or a weekend are on HomeAway.

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 HomeAway travelers, the most popular destinations to visit are:

  • Warwick: 154 vacation rentals
  • United States Military Academy: 124 vacation rentals
  • West Point: 186 vacation rentals
  • Newburgh: 533 vacation rentals
  • Greenwood Lake: 115 vacation rentals

And HomeAway 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:

  • Warwick: 154 rentals
  • West Point: 186 rentals
  • Newburgh: 533 rentals
  • Greenwood Lake: 115 rentals
  • Middletown: 955 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): 224 vacation rentals
  • Orange County Airport (MGJ): 216 vacation rentals
  • Poughkeepsie, NY (POU-Dutchess County): 268 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?

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

  • United States Military Academy: 124 rentals
  • Woodbury Common Premium Outlets: 186 rentals
  • Storm King State Park: 181 rentals
  • Warwick Valley Winery and Distillery: 177 rentals
  • Mount Peter Ski Area: 200 rentals

But there are many other points of interest around Orange County listed on HomeAway 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

154 vacation rentals
West Point
186 vacation rentals
533 vacation rentals
Greenwood Lake
115 vacation rentals
955 vacation rentals
Highland Falls
159 vacation rentals
248 vacation rentals
Tuxedo Park
94 vacation rentals
64 vacation rentals
Port Jervis
45 vacation rentals
50 vacation rentals
New Windsor
119 vacation rentals
137 vacation rentals
54 vacation rentals
83 vacation rentals
77 vacation rentals
Orange Lake
61 vacation rentals
88 vacation rentals
Fort Montgomery
85 vacation rentals
Beaverdam Lake-Salisbury Mills
99 vacation rentals