Default HTG hotel image

New Windsor Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for New Windsor vacation rentals

A living room with a brown leather sofa, a brown leather chair, a TV on a stand, and a painting on the wall.

1. < 1 Mi to Main St: Quiet Apartment in Galesburg!

< 1 Mi to Main St: Quiet Apartment in Galesburg!
2.5 star property
Galesburg
$205 nightly
The price is $240
Oct 25 - Oct 26
Total with taxes and fees
< 1 Mi to Main St: Quiet Apartment in Galesburg!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

Private Cabin Retreat with Hot Tub, Fire Pit & Gas Log Fireplace

Private Cabin Retreat with Hot Tub, Fire Pit & Gas Log Fireplace

10/10 Excellent
"We stayed in this cute cabin for the Iowa vs Ohio State football game. Ben was a great host and communication was top notch! The cabin was clean and well stocked. Loved the fact we didn't have to go out to a store right away to stock up on necessities. Kitchen had everything we needed for our stay. There was plenty of room for the 6 of us. We felt safe and secluded on the property. Even had a couple of deer visit us in the morning. Loved the fact that there was a binder with lots of information in it for the cabin and the surrounding area. It is a cozy little cabin but fit our needs perfectly."
Jolene S. 3-night trip
Posted 17 hours ago
Private Cabin Retreat with Hot Tub, Fire Pit & Gas Log Fireplace

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $240 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in New Windsor?

Yes, you can find vacation rentals close to top sights in New Windsor, or you can select a more remote option if you're looking for relaxation.

What's the top vacation rental that New Windsor has to offer?

Charming 2-bedroom house in historical Galesburg neighborhood : This vacation home near New Windsor is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in New Windsor?

While exploring the area, visit family-friendly sights like Lakeside Water Park, or get outside and enjoy nature at Lake Storey. In the larger area, you’ll find Creekside Vineyards and Carl Sandburg College.

What are vacation rentals like in New Windsor?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in New Windsor. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.