New Windsor Vacation Rentals

Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for New Windsor vacation rentals

1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (27 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
$181 nightly
The price is $192
Feb 11 - Feb 12
Total with taxes and fees
Cozy, dog-friendly, downtown
Smart TV

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
$173 nightly
The price is $184
Feb 11 - Feb 12
Total with taxes and fees
Pet-friendly, heart of downtown
Fridge, microwave, coffee/tea maker, toaster

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.
$188 nightly
The price is $199
Feb 9 - Feb 10
Total with taxes and fees
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
TV, foosball, books

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.
$160 nightly
The price is $170
Feb 6 - Feb 7
Total with taxes and fees
Cozy Pine Tree Nest
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
$144 nightly
The price is $153
Feb 6 - Feb 7
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay. The place has perfect and the location was close to everything downtown. The host was great. Will definitely stay there again."
United States
Patrick H.
$246 nightly
The price is $261
Feb 17 - Feb 18
Total with taxes and fees
Chic, pets, walk to downtown
Outdoor dining

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)
"Everything was very clean and tidy, and very bright. The beds were extremely comfortable. Location was perfect and we really enjoyed having the backyard with a hot tub and a fire pit very relaxing."
United States
Donna C.
$236 nightly
The price is $250
Feb 8 - Feb 9
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Pool

Applewood Landing

Applewood Landing
Gettysburg
10.0 out of 10, Exceptional, (10 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 traveler
$780 nightly
The price is $827
Feb 9 - Feb 10
Total with taxes and fees
Applewood Landing
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (78 reviews)
"Great location and has exactly what you need to enjoy a stay in downtown Frederick!"
United States
Amy R.
$248 nightly
The price is $263
Feb 8 - Feb 9
Total with taxes and fees
*Modern Condo In Downtown Frederick*
Exterior detail

Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (7 reviews)
"The appartment was lovely and the location was great. The parking was a struggle, but all city locations are. I would definitely recommend staying here."
United States
Ashley B.
$211 nightly
The price is $224
Mar 4 - Mar 5
Total with taxes and fees
Huge 1br apt, baby-friendly, dogs, walkable downtown
TV

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
$257 nightly
The price is $284
Feb 6 - Feb 7
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Dining

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
$245 nightly
The price is $260
Feb 8 - Feb 9
Total with taxes and fees
*Luxury Condo In Downtown Frederick*
Living area

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
$119 nightly
The price is $131
Feb 6 - Feb 7
Total with taxes and fees
Cozy studio charming Hanover
Terrace/patio

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.
$321 nightly
The price is $340
Feb 8 - Feb 9
Total with taxes and fees
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Smart TV, computer monitors

Walkable Downtown Loft - 9 Min Walk To Carroll Creek With Two Parking Spots

Walkable Downtown Loft - 9 Min Walk To Carroll Creek With Two Parking Spots
Frederick
10.0 out of 10, Exceptional, (3 reviews)
"Clean, adorably decorated. Even the pull out bed was comfortable. So close to downtown Frederick. Great communication with the owners. "
United States
Jodi C.
Walkable Downtown Loft - 9 Min Walk To Carroll Creek With Two Parking Spots
Fridge, microwave, oven, stovetop

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)
"Wonderful first experience with VRBO. Our hosts were very friendly and made our stay comfortable. "
United States
Janis O.
$315 nightly
The price is $348
Feb 19 - Feb 20
Total with taxes and fees
Charming 4-bedroom house with WiFi and AC in historic Gettysburg
Fridge, microwave, oven, stovetop

Gated 3BR Apartment in Westminster Private Parking

Gated 3BR Apartment in Westminster Private Parking
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.
$279 nightly
The price is $295
Feb 7 - Feb 8
Total with taxes and fees
Gated 3BR Apartment in Westminster Private Parking
Microwave, stovetop, dishwasher

The blissful house in Howard County with 3 bedrooms 3 bathrooms.

The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Marriottsville
10.0 out of 10, Exceptional, (2 reviews)
"Very nice property, the host was responsive to my communications and we had a great stay with no issues."
United States
Jason H.
$823 nightly
The price is $872
Feb 8 - Feb 9
Total with taxes and fees
The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Dining

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)
"Great location — right on the Carroll Creek Walk and a stone’s throw from excellent restaurants and nice shops. "
United States
Darby R.
$315 nightly
The price is $334
Feb 9 - Feb 10
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Game room

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Woodbine
$148 nightly
The price is $157
Feb 10 - Feb 11
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

Marriott Owings Mills Metro Centre

Marriott Owings Mills Metro Centre

10/10 Excellent
"Absolutely lovely hotel"
Tina 1-night trip
Posted 2 days ago
Marriott Owings Mills Metro Centre

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

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

New Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $153 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

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

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 vacation rentals in New Windsor?

Yes, we give you a choice of vacation rentals near well known points of interest in New Windsor, or you can go with a more secluded option if you want a relaxing place to 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 vacation home rentals in New Windsor?

*Luxury Condo In Downtown Frederick*: Visitors like this New Windsor vacation home rental. It is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 larger area, you’ll find Old Westminster Winery and Carroll County Farm Museum.

What’s a vacation rental in New Windsor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in New Windsor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.