New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

Fall is right around the corner! Plan your mountain getaway now!
10.0 out of 10, Exceptional, (309)
"Great cabin. Have visited numerous time for golf trips. Works great for a foursome. 4 distinct sleeping areas, well stocked, great front porch. We’ll be back. "
United States
Jim G.
Fall is right around the corner! Plan your mountain getaway now!
*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. "
United States
Michael B.
The price is AU$411
includes taxes & fees
4 Nov - 5 Nov
*Modern Condo In Downtown Frederick*
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (123)
"Location, location, location! Convenient, clean, cozy, well-equipped, wonderful view from a very comfortable porch.Great hospitality by the owners - a nice welcome, juices, water, coffee, and delicious scones."
United States
Bob W.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
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! "
United States
WILLIAM T.
ROMANTIC GETAWAY : Relax In Our Outdoor Spa This Winter !
Manor on the 7th Luxury minutes away from History
9.8 out of 10, Exceptional, (17)
"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. "
United States
Thomas P.
Manor on the 7th Luxury minutes away from History
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. "
United States
Dustin
The price is AU$411
includes taxes & fees
2 Nov - 3 Nov
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Birch Cabin at Hunting Creek Hideaway
9.8 out of 10, Exceptional, (15)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
United States
Julie B.
The price is AU$215
includes taxes & fees
7 Nov - 8 Nov
Birch Cabin at Hunting Creek Hideaway
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. "
United States
Thomas d.
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
*Luxury Condo In Downtown Frederick*
9.0 out of 10, Wonderful, (68)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is AU$407
includes taxes & fees
4 Nov - 5 Nov
*Luxury Condo In Downtown Frederick*
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!"
United States
Karen K.
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
10.0 out of 10, Exceptional, (5)
"Very nice place .Quiet and peaceful"
United States
Lisa O.
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
8.0 out of 10, Very good, (1)
"This was a great location for two families coming together for a wedding. The beds were comfortable, and the house was conveniently located within walking distance of a shopping plaza and close to the expressway on-ramp. The owner was quick to respond and helpful in answering any questions we had.Overall, the house met all our needs and provided a comfortable stay. It could use a few minor updates—like fresh paint on the scuffed walls—and some additional seating since it sleeps nine people....
United States
Heather P.
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby
A View of the Middletown Valley Like No Other
9.6 out of 10, Exceptional, (24)
"Quaint home overlooking the valley. Comfortable. Location was just right. "
United States
Penny C.
A View of the Middletown Valley Like No Other
19th Century Mansion/Farm House
10.0 out of 10, Exceptional, (43)
"Great stay again! Mike is a great host and the place works great for a golf weekend with eight buddies!Well equipped place with interesting history."
United States
Adam M.
19th Century Mansion/Farm House
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (57)
"We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. "
United States
Karen B.
The price is AU$388
includes taxes & fees
29 Oct - 30 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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!"
United States
Kristen C.
Sunlight 2BR townhouse w/ private parking in Downtown Frederick
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. "
United States
Anonymous traveller
The Jarboe Suite on historic Manor House grounds!
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. "
United States
robert M.
Quiet, Safe Nest-Minutes to Everything
Charming 4-bedroom house with WiFi and AC in historic Gettysburg
10.0 out of 10, Exceptional, (2)
"Wonderful first experience with VRBO. Our hosts were very friendly and made our stay comfortable. "
United States
Janis O.
The price is AU$833
includes taxes & fees
4 Nov - 5 Nov
Charming 4-bedroom house with WiFi and AC in historic Gettysburg
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
9.8 out of 10, Exceptional, (49)
"Awesome place."
United States
Holly J.
The price is AU$712
includes taxes & fees
2 Nov - 3 Nov
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
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

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. 

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.