New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in New Windsor

Fridge, microwave, oven, stovetop
Fall is right around the corner! Plan your mountain getaway now!
Fall is right around the corner! Plan your mountain getaway now!
10.0 out of 10, Exceptional, (308)
"We had a great time.The cabin was very clean and cozy. We loved using the fireplace!"
Fall is right around the corner! Plan your mountain getaway now!
Property grounds
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (121)
"The cabin was cozy, clean, well stocked with essientials, and additional gifts (i.e. coffee pods, personal pizzas, and breakfast scones). It was perfect! 10/10 for the accommodations! We will be stayinf again!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Fridge, microwave, oven, stovetop
*Modern Condo In Downtown Frederick*
*Modern Condo In Downtown Frederick*
9.4 out of 10, Exceptional, (72)
"It was clean and spacious, had some items that we did not expect like coffee and cream, which helped in the morning. Will book again on our next visit to this area. "
The price is AU$413
includes taxes & fees
19 Oct - 20 Oct
*Modern Condo In Downtown Frederick*
Property grounds
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
10.0 out of 10, Exceptional, (143)
"We will be back! The guest house was perfect for us! "
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Pool
Manor on the 7th Luxury minutes away from History
Manor on the 7th Luxury minutes away from History
9.8 out of 10, Exceptional, (16)
"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
Smart TV
*Luxury Condo In Downtown Frederick*
*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (68)
"Great time. Everything was perfect and place was just what we needed. "
The price is AU$408
includes taxes & fees
20 Oct - 21 Oct
*Luxury Condo In Downtown Frederick*
Property grounds
Birch Cabin at Hunting Creek Hideaway
Birch Cabin at Hunting Creek Hideaway
9.8 out of 10, Exceptional, (13)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is AU$215
includes taxes & fees
20 Oct - 21 Oct
Birch Cabin at Hunting Creek Hideaway
Fridge, microwave, oven, stovetop
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
10.0 out of 10, Exceptional, (1)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
The price is AU$411
includes taxes & fees
16 Oct - 17 Oct
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
9.8 out of 10, Exceptional, (30)
"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "
The price is AU$404
includes taxes & fees
20 Oct - 21 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Pool
Applewood Landing Sum
Applewood Landing Sum
10.0 out of 10, Exceptional, (6)
"Family of 9 had a great time at this beautiful home with room to spare! "
The price is AU$1,451
includes taxes & fees
4 Nov - 5 Nov
Applewood Landing Sum
Exterior
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
The price is AU$532
includes taxes & fees
16 Oct - 17 Oct
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
Smart TV
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
9.8 out of 10, Exceptional, (20)
"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
Interior
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
9.4 out of 10, Exceptional, (38)
"Great time, owner very attentive! Thank you!"
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Fridge, microwave, oven, stovetop
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
10.0 out of 10, Exceptional, (4)
"Very nice place .Quiet and peaceful"
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Outdoor dining
A View of the Middletown Valley Like No Other
A View of the Middletown Valley Like No Other
9.6 out of 10, Exceptional, (24)
"Great location and accommodations. The host (Greg) lives next door and could not have been more responsive and helpful!"
A View of the Middletown Valley Like No Other
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (55)
"The house was clean and the beds were very comfortable! Great stay overall "
The price is AU$352
includes taxes & fees
20 Oct - 21 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Terrace/patio
The Jarboe Suite on historic Manor House grounds!
The Jarboe Suite on historic Manor House grounds!
10.0 out of 10, Exceptional, (3)
"Has everything one needs. A little trouble with the heating system but the host was quick to respond. Would stay again. "
The Jarboe Suite on historic Manor House grounds!
Fridge, microwave, oven, stovetop
Sunlight 2BR townhouse w/ private parking in Downtown Frederick
Sunlight 2BR townhouse w/ private parking in Downtown Frederick
9.4 out of 10, Exceptional, (25)
"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
Property grounds
Quiet, Safe Nest-Minutes to Everything
Quiet, Safe Nest-Minutes to Everything
9.8 out of 10, Exceptional, (10)
"Getting too see our son and grandson was wonderful. We had a great stay thank you. "
Quiet, Safe Nest-Minutes to Everything
Property grounds
Cozy out of the way studio retreat with AC and WiFi in charming Westminster
Cozy out of the way studio retreat with AC and WiFi in charming Westminster
10.0 out of 10, Exceptional, (5)
"Great instructions, kind host, great stay!"
The price is AU$240
includes taxes & fees
20 Oct - 21 Oct
Cozy out of the way studio retreat with AC and WiFi in charming Westminster
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

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Our room was very clean. The staff was very nice and helpful. "
Amelia 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about New Windsor

Everything you need to know about New Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

New Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Windsor holiday rentals we have selected for you start as low as AU$215 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor holiday 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 holiday.

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

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?

Manor on the 7th Luxury minutes away from History: This holiday home rental outside of New Windsor is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.