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, (121)
"Good location "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

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

Round Top Campground

2.0 star property
9.0 out of 10, Wonderful, (21)
"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! "
Round Top Campground

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

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 NZ$438
includes taxes & fees
8 Oct - 9 Oct
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

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

10.0 out of 10, Exceptional, (307)
"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!

Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby

The price is NZ$554
includes taxes & fees
5 Nov - 6 Nov
Easy Self Check-in 4BR Escape • Prime Walkable Location • Dining & Shops Nearby

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 NZ$1,632
includes taxes & fees
21 Oct - 22 Oct
Applewood Landing Sum

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 NZ$452
includes taxes & fees
12 Oct - 13 Oct
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

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 !

Birch Cabin at Hunting Creek Hideaway

9.8 out of 10, Exceptional, (12)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is NZ$237
includes taxes & fees
8 Oct - 9 Oct
Birch Cabin at Hunting Creek Hideaway

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (67)
"Great time. Everything was perfect and place was just what we needed. "
The price is NZ$448
includes taxes & fees
3 Nov - 4 Nov
*Luxury Condo In Downtown Frederick*

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 NZ$782
includes taxes & fees
12 Oct - 13 Oct
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Countryside Manor |Porch, Firepit & Playset

2.0 star property
9.8 out of 10, Exceptional, (9)
"Very comfortable stay for our family! "
Countryside Manor |Porch, Firepit & Playset

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

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!

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 NZ$379
includes taxes & fees
13 Oct - 14 Oct
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

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 NZ$494
includes taxes & fees
19 Oct - 20 Oct
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

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
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 favorite 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 depends 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 NZ$237 per night. Entering your travel dates in the search wizard you might find 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.