New Windsor Holiday Rentals

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Holiday Rentals in New Windsor

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (119)
"We LOVED our stay at Surrey Cabin! Quaint, clean, quiet, and the property is breathtaking! The bed was super comfortable and we had everything we needed. We will definitely be coming back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Birch Cabin at Hunting Creek Hideaway

9.8 out of 10, Exceptional, (11)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is AU$210
includes taxes & fees
21 Sept - 22 Sept
Birch Cabin at Hunting Creek Hideaway

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

9.8 out of 10, Exceptional, (18)
"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

Manor on the 7th Luxury minutes away from History

10.0 out of 10, Exceptional, (15)
"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

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$1,405
includes taxes & fees
23 Sept - 24 Sept
Applewood Landing Sum

Fall is right around the corner! Plan your mountain getaway now!

10.0 out of 10, Exceptional, (305)
"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!

The Madison

10.0 out of 10, Exceptional, (35)
"We stayed for a week to tour college campuses for our son and are also considering moving there. We felt at home at The Madison and in the community. The house is exactly as described and in a great location to experience Frederick. "
The Madison

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

9.8 out of 10, Exceptional, (48)
"Awesome place."
The price is AU$697
includes taxes & fees
28 Sept - 29 Sept
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (67)
"Wonderful space, perfect for our family, accurate description and depiction. "
The price is AU$510
includes taxes & fees
22 Sept - 23 Sept
*Luxury Condo In Downtown Frederick*

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

9.4 out of 10, Exceptional, (115)
"Clean and comfortable, quiet and perfectly located, this the perfect place for enjoying downtown "
The price is AU$438
includes taxes & fees
21 Sept - 22 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.4 out of 10, Exceptional, (22)
"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

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (146)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown

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"
The price is AU$335
includes taxes & fees
21 Sept - 22 Sept
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

10.0 out of 10, Exceptional, (75)
"The stay was great! The house was exactly as described. Danny was super responsive and accommodating. Overall would stay again!"
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

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 !

Updated 3BR Apartment in Westminster – Family Friendly

4.0 out of 10, (1)
"This property is a bit mislisted. It is on the backside and above a commercial building. There was commercial equipment in the back, lots of trash on the lot including piles of pallets, and construction material. Its on the side of a multilane highway so it is loud at night. It would likely be fine for older kids or adults but not a good fit for young kids. The gate code was not sent along, so we had to wait to access the property until the owner got back to me (which was within 2 hours and he...
Updated 3BR Apartment in Westminster – Family Friendly

The Manor at Open Range Stables

2.0 star property
9.8 out of 10, Exceptional, (8)
"Very comfortable stay for our family! "
The Manor at Open Range Stables

Cozy, dog-friendly, downtown

10.0 out of 10, Exceptional, (25)
"Super cute and was the PERFECT location! We had a great stay! "
The price is AU$293
includes taxes & fees
30 Sept - 1 Oct
Cozy, dog-friendly, downtown

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (87)
"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

Farmhouse on River, 12 Miles to Liberty Mountain

2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful property, excellent stay! "
Farmhouse on River, 12 Miles to Liberty Mountain
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

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$210 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.