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New Windsor holiday lettings

We found 234 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of holiday rentals in New Windsor that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, pools, gardens 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. Travellers especially like the shopping, restaurants and lake in this welcoming and scenic city. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around New Windsor

Do you want to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes New Windsor a fun spot to go on holiday. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 an adventurous traveller or just want to take in the scenery, New Windsor is a great place to get outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around New Windsor

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 3.6 mi (5.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying 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 holiday rental?

One of the most desired areas to book a holiday 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 holiday rental accommodation in New Windsor?

Based on our research, apartments are the most popular holiday rental type in New Windsor. But as you'd expect, everyone's idea of the perfect stay can differ. Vrbo has holiday 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 holiday rental in New Windsor?

Length of stay, season and property type are among the factors that can determine the price of a holiday home. Simply enter your travel dates to find the ultimate escape. From cosy country cottages to sprawling villas, all Vrbo holiday 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 holiday rentals in New Windsor?

Pack a squeezy toy and a bone for your puppy dog because New Windsor has three holiday 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 holiday 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 holiday 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 holiday rentals in New Windsor that welcome kids?

New Windsor has three family-friendly holiday 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 holiday rentals in New Windsor?

Choose from two two-bedroom holiday 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 holiday rentals with WiFi in New Windsor?

You can pick from three holiday rentals with WiFi in New Windsor. If you'd like to disconnect from daily life on your holiday, 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 holiday rentals with air conditioning in New Windsor?

New Windsor has three holiday 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 holiday rental in New Windsor?

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

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