Discover a selection of 190 vacation rentals in New Windsor, NY 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 private pools. Prices start at $125 per night, and houses and condos are popular options for a stay in New Windsor. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — New Windsor
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Destination guide

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.

Things to do

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)
  • Putnam County Golf Course (15 mi / 24.2 km)
  • LEGOLAND® New York (16.5 mi / 26.6 km)
Natural features

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:

  • Bowdoin Park (9.6 mi / 15.4 km)
  • Bear Mountain State Park (12.3 mi / 19.7 km)
  • Orange County Arboretum (12.9 mi / 20.7 km)
  • The Rock Sports Complex (16 mi / 25.7 km)
  • Lake Mahopac (16 mi / 25.8 km)
  • Walkway Over the Hudson State Historic Park (16.7 mi / 26.8 km)
How to get there

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 Westchester County Airport (HPN), which is 32.7 mi (52.6 km) away.

What are the top vacation rentals in or near New Windsor?

The heart wants what the heart wants, and right now it's craving a vacation. It's time to pack your bags and take off to one of these top vacation rentals in or near New Windsor:

  • "Private Lakefront Home With Kayaks Stunning Sunsets Panoramic View" is popular with guests. Around 6 miles from New Windsor, it has 2 bedrooms and plenty of useful amenities, including a lake view and outdoor furniture.
  • "Are Available For Longer Stays Early Bookings Are Accepted" also promises a memorable getaway, offering 4 bedrooms, heating, a dining table and more. It's around 20 miles from New Windsor.

For even more great options, use the search bar at the top of the page to find the perfect New Windsor vacation rental for you.

Can I find log cabins to rent in or near New Windsor?

You bet! From rustic hideaways to high-end escapes, Vrbo has a wide range of log cabins to rent in or near New Windsor. If you're into adventure, check out:

  • "Cozy Log Cabin In Hudson Valley": Enjoy a few days relaxing and resting at this terrific escape in nature. When you've recharged, enjoy golf or fishing, which are some of the best activities in this region.
  • "Beautiful Log Cabin Style House": After a big day of trying out some local activities, such as fishing and hiking and biking, return home to this charming getaway.

What are the top-rated vacation rentals for weekend getaways in or near New Windsor?

Get far away from the daily grind at one of our weekend getaways in or near New Windsor. Whether you'd like to hang out with buddies or spend time with the family, we'll have something to suit your needs. These top-rated options are hard to beat:

  • "Beautiful Cozy 2 Bedroom In - Law Apt" is ideal for a couple of days of enjoyment and rest. It offers convenient amenities, such as off-street parking options and free toiletries, and is located around 1 mile to the east of New Windsor.
  • Otherwise, create new memories with your gang at "Guests State The Home Is Charming. New Central Air Conditioning", which is around 2 miles to the southeast of New Windsor. Take advantage of coffee and tea making facilities, a fridge and more here.

Can I find studio apartments for rent in and around New Windsor?

Yes, you can. If you'd like a simple but stylish stay, you can't top a studio apartment. These compact properties exude charm and are often conveniently placed in the center of town. Take a look at the following options in or near New Windsor:

  • After an exciting day of urban exploration, kick back and relax at "Guests State The Home Is Charming. New Central Air Conditioning". A porch and cable/satellite TV services are just some of the amenities you'll find here.
  • "Hudson River Retreat" is another top choice, providing all you could need for a great New Windsor retreat. Convenient amenities here include cable/satellite TV services and coffee and tea making facilities.

Can I find short term rentals in or near New Windsor?

Whether you're chasing a chic apartment or a house big enough to fit the family, you'll find the ideal place on Vrbo. Treat yourself to a mini break at one of these getaways in or near New Windsor:

  • For a wonderful night or two away, you can't go wrong with "Private Hudson Valley Retreat In A Parklike Setting". It's close to the center of New Windsor, in addition to lots of things to put on your itinerary.
  • Another excellent option is "Huge Home For Huge Fun - Ny Fun". Gather a few friends and enjoy a comfy stay near the heart of New Windsor.

What are the best romantic weekend getaways in or near New Windsor?

Nothing says "I love you" like planning a romantic weekend together. If you're longing to spend a couple of evenings away with your significant other, we've got some romantic getaways in and around New Windsor that will set your heart aflutter:

  • Sneak away on Friday for a few nights of passion at "Private Lakefront Home With Kayaks Stunning Sunsets Panoramic View". Located around 6 miles from New Windsor, this property comes with plenty of nice touches, including beauty services and winery tours.
  • Another place where you can enjoy a few precious days together is "Are Available For Longer Stays Early Bookings Are Accepted". Located around 20 miles from New Windsor, beauty services and a fireplace add to the atmosphere here.

Are there mansions for rent in or near New Windsor?

We've got some impressive mansions for rent in and near New Windsor. If you're looking for somewhere with lots of room as well as loads of wow factor, these architectural stunners will tick your boxes:

  • Elegance, charm and oodles of character — "West Point Mansion: New York City's Luxury Retreat" has it all. Around 3 miles southeast of New Windsor and offering a swimming pool and golf, this place is hard to beat.
  • Alternatively, step your vacation up a notch and spend a week at "Mansion House With A Pool And Tennis In 5000 Sqft". It's approximately 25 miles to the west of New Windsor and offers amenities like a firepit, a swimming pool and more.

What are the best large group vacation rentals in or near New Windsor?

Peep these large group vacation rentals in or near New Windsor and forget about leaving anyone off your invite list:

  • You'll have loads of space to sprawl out at "The Big House" With Hudson River Views". Around 6 miles northeast of New Windsor, this generous property has 8 bedrooms and sleeps up to 16 guests. It comes with a host of amenities, including a water view and a swimming pool.
  • Nothing is more important than being together with loved ones, and "Large, Cozy, Bright Business Class Corporate Retreat" makes it easy to do that. Located around 6 miles to the northeast of New Windsor, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A kitchen and a garden are among the numerous amenities on offer here.

What are the best houses for rent with a pool in or near New Windsor?

A pool is often a must-have amenity when deciding where to stay on vacation, particularly if you're traveling with kids who are full of beans. Browse these houses with a pool in or near New Windsor and spend your days splish-splashing around:

  • Pack your swimming gear and take your gang to "Hudson Valley Sunset House - Grill | Fire Pit | Hiking". There are also lots of other convenient amenities here, including a living room and a TV.
  • "The Big House" With Hudson River Views" is the type of place you go to leave it all behind and appreciate your surroundings, starting with its pool. A separate dining area and a barbecue grill are also on hand to make your stay as comfortable as possible.

Not sure what the weather's like in New Windsor? It has a humid continental climate, with average summertime temperatures ranging from 60 ºF to 80 ºF. If you're after a little more inspiration on where to stay in this amazing destination, use the search bar at the top of the page and adjust the filters to check out our entire selection of New Windsor vacation rentals.

What are the best large family vacation rentals in or near New Windsor?

No matter if your idea of the perfect escape is up in the mountains or on the beach, you'll enjoy it even more if you share it with loved ones. Look up these large family vacation rentals in or near New Windsor and bring along the whole gang:

  • Located about 20 miles to the southwest of New Windsor, "Are Available For Longer Stays Early Bookings Are Accepted" has 4 bedrooms and sleeps up to 9 guests. It comes with a host of amenities, including a garden and childrens activities.
  • "Private Hudson Valley Retreat Near West Point" is another excellent option. It's around 2 miles to the southeast of New Windsor, has 4 bedrooms and can accommodate up to 8 guests. Handy amenities here include a smart TV and a fridge.

If you're looking for family-friendly attractions in the area, there's no shortage of choice. Orange County Fairgrounds, Castle Fun Center and Harness Racing Museum and Hall of Fame offer fun for both kids and grown-ups.