New Windsor Holiday Rentals

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Our top choices for New Windsor holiday rentals

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is NZ$327
includes taxes & fees
12 Jan - 13 Jan
Pet-friendly, heart of downtown

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (26 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$335
includes taxes & fees
14 Jan - 15 Jan
Cozy, dog-friendly, downtown

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.4 out of 10, Exceptional, (3 reviews)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
The price is NZ$432
includes taxes & fees
11 Jan - 12 Jan
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
The price is NZ$296
includes taxes & fees
12 Jan - 13 Jan
Cozy Pine Tree Nest

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (19 reviews)
"It was a fabulous stay, and Brittany, the host, was very helpful with bringing a gas grill, AC, and communication. The scenery is very beautiful and it's very quiet. Great place for a hiking getaway."
United States
Fr. Andrew H.
The price is NZ$265
includes taxes & fees
19 Jan - 20 Jan
Birch Cabin at Hunting Creek Hideaway

Saadallah Cozy-ta

Saadallah Cozy-ta
2.0 star property
Glenwood
The price is NZ$170
includes taxes & fees
11 Jan - 12 Jan
Saadallah Cozy-ta

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (72 reviews)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is NZ$451
includes taxes & fees
11 Jan - 12 Jan
*Luxury Condo In Downtown Frederick*

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62 reviews)
"Always clean and comfortable home. Close to restaurants and shops but in quiet neighborhood to relax. Our second stay in this home. "
United States
Jelinda C.
The price is NZ$450
includes taxes & fees
11 Jan - 12 Jan
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Charming 4-bedroom house with WiFi and AC in historic Gettysburg

Charming 4-bedroom house with WiFi and AC in historic Gettysburg
Gettysburg
10.0 out of 10, Exceptional, (3 reviews)
"Very clean home, quiet neighborhood, and close to town. The blueberry muffins were an added delight"
United States
Gail D.
The price is NZ$590
includes taxes & fees
9 Feb - 10 Feb
Charming 4-bedroom house with WiFi and AC in historic Gettysburg

Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes
Ijamsville
10.0 out of 10, Exceptional, (5 reviews)
"Good trip."
United States
Jewell F.
The price is NZ$625
includes taxes & fees
14 Jan - 15 Jan
Cozy Peaceful Basement Cabin Vibes

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
The price is NZ$435
includes taxes & fees
11 Jan - 12 Jan
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (14 reviews)
"This is our second time staying here and we really love how easily we all fit in. It's clean, family friendly, and have lots of space."
United States
Bonnie S.
The price is NZ$607
includes taxes & fees
12 Jan - 13 Jan
Newly constructed 6 bedroom home

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (9 reviews)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
The price is NZ$624
includes taxes & fees
11 Jan - 12 Jan
New townhouse

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (76 reviews)
"Great location and has exactly what you need to enjoy a stay in downtown Frederick!"
United States
Amy R.
The price is NZ$457
includes taxes & fees
1 Feb - 2 Feb
*Modern Condo In Downtown Frederick*

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (120 reviews)
"Excellent location for our family wedding weekend! We walked to all the events of the weekend."
United States
Cynthia L.
The price is NZ$531
includes taxes & fees
11 Jan - 12 Jan
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Applewood Landing

Applewood Landing
Gettysburg
10.0 out of 10, Exceptional, (8 reviews)
"Perfect home for our family of 14 celebrating my mom’s 80th! Spacious kitchen with two dishwashers, great pool area, and plenty of room to gather. Loved the sunsets, outdoor amenities, and convenient location. Hosts were wonderful and responsive—highly recommend!"
United States
Anonymous traveller
The price is NZ$1,498
includes taxes & fees
13 Jan - 14 Jan
Applewood Landing

Updated 3BR Apartment in Westminster – Family Friendly

Updated 3BR Apartment in Westminster – Family Friendly
Westminster
8.0 out of 10, Very good, (5 reviews)
"Had a great stay here for a night. Was a good size for the four people we had stay. Beds were comfortable and the house was clean. "
United States
John M.
The price is NZ$511
includes taxes & fees
11 Jan - 12 Jan
Updated 3BR Apartment in Westminster – Family Friendly

Experience Elevated Comfort: Luxe Breeze Townhouse.

Experience Elevated Comfort: Luxe Breeze Townhouse.
Owings Mills
9.6 out of 10, Exceptional, (4 reviews)
"Awesome stay and great location. Very quiet neighborhood, made the stay comfortable and relaxing. Very spacious and modern. "
United States
Jesse H.
The price is NZ$975
includes taxes & fees
2 Feb - 3 Feb
Experience Elevated Comfort: Luxe Breeze Townhouse.

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Westminster
9.0 out of 10, Wonderful, (2 reviews)
"The stay was nice and as advertised. It was a little noisy at night with the split house and close neighbors, but it was a nice place. "
United States
Payson D.
The price is NZ$583
includes taxes & fees
22 Jan - 23 Jan
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
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 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$265 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?

The blissful house in Howard County with 3 bedrooms 3 bathrooms.: This holiday home rental outside of New Windsor offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.