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New Windsor vacation rentals

We found 232 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
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.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

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. 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:

  • 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)
  • Castle Fun Center (15.7 mi / 25.3 km)
  • LEGOLAND® New York (16.5 mi / 26.6 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)
  • Hudson Highlands State Park (4.3 mi / 7 km)
  • Clarence Fahnestock State Park (10.3 mi / 16.6 km)
  • Bear Mountain State Park (12.3 mi / 19.7 km)
  • The Rock Sports Complex (16 mi / 25.7 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?

One of the most desired areas to book a vacation rental in New Windsor is Vails Gate. Find the perfect stay with Vrbo and explore this area like a local.

What is the most popular type of vacation rental accommodation in New Windsor?

Based on our research, apartments are the most popular vacation rental type in New Windsor. But as you'd expect, everyone's idea of the perfect stay can differ. Vrbo has vacation rentals with every size, shape and budget in mind, and we'll help you to find your ideal fit.

How much does it cost to rent a vacation rental in New Windsor?

Length of stay, season and property type are among the factors that can determine the price of a vacation home. Simply enter your travel dates to find the ultimate escape. From cozy country cottages to sprawling villas, all Vrbo vacation rentals offer amazing value.

How much does it cost to rent a beach house in New Windsor?

Prices for beach houses in New Windsor may differ depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to see your options and prices. From there you can use our filters to refine your search results by ratings, amenities, nearby activities and more.

Are there pet-friendly vacation rentals in New Windsor?

Pack a squeezy toy and a bone for your puppy dog because New Windsor has three vacation rentals that roll out the welcome mat to pets. Let your furriest pal join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.

What are popular rental amenities in New Windsor?

When it comes to rental amenities that guests are looking for in New Windsor, a barbecue grill, a garden and a nearby river rank the highest. With Vrbo vacation rentals, you'll enjoy options to suit your taste and style, whether you're going on a trip with relatives, friends or even pets.

Are there vacation rentals in New Windsor that welcome kids?

New Windsor has three family-friendly vacation homes. And tracking down a stay that welcomes youngsters is simple with Vrbo's "Properties good for families" filter. In addition to having the whole place to yourselves, you'll get access to amenities and perks such as extra bedrooms, full kitchens and yards.

What are the top attractions for families in New Windsor?

You'll find lots of amazing things to see and do with the family in New Windsor, including:

  • SplashDown Beach
  • Motorcyclepedia Museum
  • Hudson Highlands Nature Museum

Can I find two-bedroom vacation rentals in New Windsor?

Choose from two two-bedroom vacation properties in New Windsor. Put the kids in the second room or fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.

Are there vacation rentals with WiFi in New Windsor?

You can pick from three vacation rentals with WiFi in New Windsor. If you'd like to disconnect from daily life on your vacation, but still want to be connected to the web, these properties have just 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?

New Windsor has three vacation rentals where you can kick back in air-conditioned comfort. To find a property on Vrbo that features this amenity, enter your dates of travel and use the handy filter tool to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in New Windsor?

It's advisable to check with the New Windsor vacation property you're considering on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.

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