New Windsor Vacation Rentals from ￥12,632: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in New Windsor?

Gorgeous 1840 Log Cabin- Downtown : You might want to consider this vacation home rental near New Windsor, which is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in New Windsor

"This is an amazing place to stay its not far away from alot of things but gives you the sense of being in the middle of no where. "

"Very nice place .Quiet and peaceful"

￥33,148 total

includes taxes & fees

Aug 17 - Aug 18

"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "

"Great stay "

￥47,131 total

includes taxes & fees

Aug 26 - Aug 27

"Best place to get away from all the city CHAOS in Washington, DC!"

Cottage, 2 Bedrooms (Loft, No Pets) | WiFi

"Campground is short drive to many of Gettysburg's tours and museums. It also has structured activities for families/kids. And also hosts food trucks! "

"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "

"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."

￥49,958 total

includes taxes & fees

Sep 2 - Sep 3

"Cabin was perfect! So cute! We loved it and will definitely stay there again! "

￥20,437 total

includes taxes & fees

Aug 13 - Aug 14

"The location was perfect for walking just about anywhere we needed to go! Two bedrooms were a plus for me, my husband, and his sister. The half bath downstairs was also appreciated!"

"We enjoyed our stay!"

3 bedrooms, travel crib, free WiFi, bed sheets

"My family stayed one night. It was perfect for what we needed.....clean and cozy"

￥31,500 total

includes taxes & fees

Aug 13 - Aug 14

"Our favorite spot in the Gettysburg area. The house is peaceful and comfortable, fully stocked and very well maintained. We've stay several times and have never been disappointed. The owners are very responsive, always an enjoyable stay."

"Enjoyed our stay. Very quiet and secluded after you’ve spent your day visiting Gettysburg’s museum and battlefields. "

"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"

￥42,104 total

includes taxes & fees

Sep 7 - Sep 8

"Very well decorated. The owners were very attentive and kind. Left a candle with wine in the bedrooms. Very well set up and beautiful!!"

"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "

"We had a wonderful stay. The house is just a few minutes from the Gettysburg battlefield. We spent three days touring the battlefield and the house was perfect for relaxing and unwinding at the end of each busy day. "

"Awesome place."

￥67,755 total

includes taxes & fees

Aug 13 - Aug 14

"We all had a wonderful time and the stay was amazing. Thank you for opening your home for us."

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

Hyatt Place Baltimore/Owings Mills

10/10 Excellent

" The only thing I didn’t like was the breakfast in the TV TV is way too update it"

Colton Motel Gettysburg

10/10 Excellent

"The staff was very friendly and efficient with a quick and easy check-in. I have read many of the reviews. For the people complaining, I am uncertain what guests were expecting for such a reasonable rate right in the middle of the historical area. The accommodations were nice with a comfortable bed, nice shower, working refrigerator, simple breakfast, and nice TV. The pool was relaxing and the area was quiet enough for a good night's rest. We were able to take a nice walk to get into the center of town to enjoy history, food, and shopping. For a family on a budget, this place worked out just fine."

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

View our selection of featured holiday rentals in New Windsor
Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

Look no further and take a look at our great range of rental properties in New Windsor!

Frequently asked questions

Can I find vacation rentals in New Windsor?

Yes, we give you a choice of vacation rentals near well known points of interest in New Windsor, or you can go with a more secluded option if you want a relaxing place to stay. New Windsor is known for its shopping and wineries. Make sure you have time to check out the restaurants and university setting during your trip.

What are some of the best vacation home rentals in New Windsor?

Gorgeous 1840 Log Cabin- Downtown: You might want to consider this vacation home rental near New Windsor, which is located in the city center and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in New Windsor?

While exploring the area, visit family-friendly sights like Adventure Park USA, or get outside and enjoy nature at Union Mills Homestead Park. In the larger area, you’ll find Old Westminster Winery and Elk Run Vineyards.

What’s a vacation rental in New Windsor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in New Windsor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

New Windsor Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Vacation Rentals in New Windsor

Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Gorgeous 1840 Log Cabin- Downtown

Modern Condo In Downtown Frederick

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Round Top Campground

“The Train Depot” 2nd oldest in the US

Luxury Condo In Downtown Frederick

Birch Cabin at Hunting Creek Hideaway

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

Quiet Apartment in Coolest Small Town in America!

Cozy 3-bedroom townhome in welcoming Glenwood with WiFi, AC and Park 2 min drive

3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg

Farmhouse on River, 12 Miles to Liberty Mountain

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

LAST MINUTE GETAWAY! we're offering a 15% discount due to recent cancellation!

Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick

Manor on the 7th Luxury minutes away from History

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Historic "BREECHES POCKET" Civil W Era Log House /No rentals after DEC. 31 2025