Holiday Rentals in New Windsor

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Holiday Rentals in New Windsor

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

10.0 out of 10, Exceptional, (15)
"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. "
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

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

10.0 out of 10, Exceptional, (3)
"Very nice place .Quiet and peaceful"
The price is €198
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (142)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown

*Modern Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (66)
"Great stay "
The price is €274
includes taxes & fees
2 Sept - 3 Sept
*Modern Condo In Downtown Frederick*

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (110)
"Best place to get away from all the city CHAOS in Washington, DC!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (83)
"Great location in downtown Frederick. Cozy and comfortable accommodation with great historic vibes and modern amenities. We would definitely stay here again. "
“The Train Depot” 2nd oldest in the US

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (65)
"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."
The price is €308
includes taxes & fees
26 Aug - 27 Aug
*Luxury Condo In Downtown Frederick*

Birch Cabin at Hunting Creek Hideaway

9.6 out of 10, Exceptional, (7)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is €123
includes taxes & fees
20 Aug - 21 Aug
Birch Cabin at Hunting Creek Hideaway

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.2 out of 10, Wonderful, (20)
"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!"
Sunlight 2BR townhouse w/ private parking in Downtown Frederick

Quiet Apartment in Coolest Small Town in America!

9.6 out of 10, Exceptional, (47)
"We enjoyed our stay!"
Quiet Apartment in Coolest Small Town in America!

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

8.0 out of 10, Very good, (1)
"My family stayed one night. It was perfect for what we needed.....clean and cozy"
The price is €197
includes taxes & fees
14 Aug - 15 Aug
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

10.0 out of 10, Exceptional, (304)
"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."
3-bedroom cabin in a wooded setting just 17 minutes from Gettysburg

Farmhouse on River, 12 Miles to Liberty Mountain

9.8 out of 10, Exceptional, (49)
"Enjoyed our stay. Very quiet and secluded after you’ve spent your day visiting Gettysburg’s museum and battlefields. "
Farmhouse on River, 12 Miles to Liberty Mountain

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

9.4 out of 10, Exceptional, (113)
"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"
The price is €250
includes taxes & fees
7 Sept - 8 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

10.0 out of 10, Exceptional, (141)
"Very well decorated. The owners were very attentive and kind. Left a candle with wine in the bedrooms. Very well set up and beautiful!!"
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !

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

10.0 out of 10, Exceptional, (26)
"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "
Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick

Manor on the 7th Luxury minutes away from History

10.0 out of 10, Exceptional, (14)
"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. "
Manor on the 7th Luxury minutes away from History

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

9.8 out of 10, Exceptional, (46)
"Awesome place."
The price is €401
includes taxes & fees
14 Aug - 15 Aug
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

10.0 out of 10, Exceptional, (170)
"We all had a wonderful time and the stay was amazing. Thank you for opening your home for us."
Historic "BREECHES POCKET" Civil W Era Log House /No rentals after DEC. 31 2025

Quiet, Safe Nest-Minutes to Everything

10.0 out of 10, Exceptional, (8)
"The house was perfect for us to stay during our trip to Frederick. Walking distance to a few very good restaurants, no traffic, quiet neighborhood, easy access to everything. Definitely recommend."
Quiet, Safe Nest-Minutes to Everything
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.
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Top New Windsor Hotel Reviews

Frequently asked questions

Can I find holiday rentals in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that New Windsor has to offer?

Gorgeous 1840 Log Cabin- Downtown: This holiday home rental outside of New Windsor is located in the city centre, 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 that you can cook with friends or family. Make the most 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 wider area, you’ll find Old Westminster Winery and Elk Run Vineyards.

What’s a holiday rental in New Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in New Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for small groups.