Photo by Wanderlustfemale

New Windsor vacation rentals

We found 245 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in New Windsor that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, including WiFi and parking. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

The lakeside setting of New Windsor is ready to explore

Enjoy the art galleries and other features of New Windsor. Travelers like the shopping, restaurants and lake in this welcoming and scenic city. Woodbury Common Premium Outlets and LEGOLAND® New York are just a couple of the must-sees in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around New Windsor

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes New Windsor a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® New York (16.5 mi / 26.6 km)
  • Ice Time Sports Complex (5.4 mi / 8.6 km)
  • Brotherhood Winery (7.8 mi / 12.6 km)
  • SplashDown Beach (7.8 mi / 12.6 km)
  • Benmarl Vineyards and Winery (8.3 mi / 13.4 km)
  • Putnam County Golf Course (15 mi / 24.2 km)

Exploring the natural landscape of New Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, New Windsor is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Algonquin Park (3.6 mi / 5.8 km)
  • Storm King State Park (4 mi / 6.5 km)
  • Storm King Art Center (4 mi / 6.5 km)
  • Hudson Highlands State Park (4.3 mi / 7 km)
  • Oscawana Lake (10.7 mi / 17.3 km)
  • Lake Tiorati Beach (14.3 mi / 23 km)

Traveling to and around New Windsor

The nearest airport is in Stewart Intl. Airport (SWF), located 3.6 mi (5.8 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Danbury, CT (DXR-Danbury Municipal), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the best area to stay in New Windsor when booking a vacation rental?
Among the most sought-after neighborhoods to book a vacation property in New Windsor is Vails Gate. Find your perfect stay with Vrbo and experience this area like a local.
What is the most popular type of vacation rental accommodation in New Windsor?
The most popular types of vacation rentals in New Windsor are apartments. Looking for something different? Vrbo offers a variety of options to match our guests’ unique needs, so you’ll see vacation homes in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — discover yours today.
How much does it cost to rent a vacation rental in New Windsor?
The average price for a vacation home in New Windsor is determined by a number of factors, including length of stay, season and property type. Whether you’re searching for a villa with space for extended family or a quaint cottage that’s perfect for two, just enter your dates of travel to find stays with terrific value.
How much does it cost to rent a beach house in New Windsor?
The average price for a vacation rental by the beach in New Windsor will depend on when you’re going and the size and type of property you’re looking for. You can easily and quickly find prices on Vrbo by entering your dates of travel. Then use the handy filters to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly vacation rentals in New Windsor?
Yes, there are. You’ll find three vacation rentals that allow pets in New Windsor on Vrbo. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your pup can join in the fun.
What are popular rental amenities in New Windsor?
A firepit, a barbecue grill and a nearby river are rated the most popular rental amenities in New Windsor. Whether you’re planning to travel on your own, with your other half or a bunch of friends, Vrbo will help you find a vacation home that suits your style with all the features you’ll enjoy.
Are there large group vacation rentals in New Windsor?
Take your pick of two Vrbo vacation rentals in New Windsor that can host a group of five or more guests. You’ll enjoy all the privacy and space you need to have fun with your favorite people — and no one else.
Are there vacation rentals in New Windsor that welcome kids?
New Windsor has three family-friendly vacation rentals to choose from. And tracking down a stay that welcomes kids is super easy with Vrbo’s “Properties good for families” filter. As well as having the whole place to yourselves, you’ll also get conveniences and perks such as living rooms, kitchens and private pools.
What are the top attractions for families in New Windsor?
Keeping the kids occupied during your New Windsor vacation is simple with these family-friendly attractions:

  • Kristi Babcock Memorial Park
  • National Purple Heart Hall of Honor
  • Knox’s Headquarters State Historic Site

Can I find two-bedroom vacation rentals in New Windsor?
New Windsor has two two-bedroom vacation properties for you to pick from. Experience a vacation home with all the comfort and privacy you want at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in New Windsor?
You’ll find three vacation rentals with WiFi in New Windsor. If you’d like to disconnect from the world during your trip, but still want to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in New Windsor?
Pick your travel dates and then use the filters to locate vacation rentals with ac in New Windsor on Vrbo. With three air-conditioned properties to choose from here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a vacation rental in New Windsor?
The minimum age is generally 16, 18 or 21. It can change between properties on Vrbo, so check the rules of your preferred New Windsor vacation home before booking your trip.
How long can I rent a vacation rental in New Windsor for?
The amount of time you can stay in a New Windsor vacation rental for is up to the property. Just enter your travel dates to view available options that offer long-term stays. They include all the things you need to make your extended trip more comfortable and enjoyable, like air conditioning and laundries. Some properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.
Does Vrbo offer discounts for vacation homes in New Windsor?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fabulous bargains and discounts on Vrbo. From weekend retreats to extended getaways, we’ve got the ideal space for your next New Windsor escape.

More Vacation Rentals ideas

People also search for