New Windsor Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Dec 9 - Dec 10
Tomorrow
Dec 10 - Dec 11
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for New Windsor vacation rentals

Fridge, microwave, oven, stovetop
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Cottage in Hanover

9.4 out of 10, Exceptional, (3)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
$222 nightly
The price is $245
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Fridge, microwave, coffee/tea maker, electric kettle
Cozy Pine Tree Nest

Apartment in Frederick

9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
$171 nightly
The price is $181
Dec 29 - Dec 30
Total with taxes and fees
Cozy Pine Tree Nest
Smart TV
Pet-friendly, heart of downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
$181 nightly
The price is $192
Dec 10 - Dec 11
Total with taxes and fees
Pet-friendly, heart of downtown
Fridge, microwave, oven, stovetop
Cozy, dog-friendly, downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
$186 nightly
The price is $197
Dec 10 - Dec 11
Total with taxes and fees
Cozy, dog-friendly, downtown
Property grounds
Birch Cabin at Hunting Creek Hideaway

Cabin in Thurmont

9.8 out of 10, Exceptional, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
$131 nightly
The price is $138
Dec 15 - Dec 16
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Cottage in Frederick

10.0 out of 10, Exceptional, (62)
"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.
$245 nightly
The price is $260
Dec 10 - Dec 11
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop
*Modern Condo In Downtown Frederick*

Condo in Downtown Frederick

9.4 out of 10, Exceptional, (74)
"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
Dec 14 - Dec 15
Total with taxes and fees
*Modern Condo In Downtown Frederick*
Smart TV
*Luxury Condo In Downtown Frederick*

Vacation Home in Downtown Frederick

9.0 out of 10, Wonderful, (71)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
$247 nightly
The price is $262
Dec 10 - Dec 11
Total with taxes and fees
*Luxury Condo In Downtown Frederick*
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Vacation Home in Downtown Frederick

9.4 out of 10, Exceptional, (119)
"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "
United States
Natalie C.
$261 nightly
The price is $277
Dec 14 - Dec 15
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Vacation Home in Frederick

10.0 out of 10, Exceptional, (34)
"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.
$242 nightly
The price is $257
Jan 7 - Jan 8, 2026
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Outdoor spa tub
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

Vacation Home in Westminster

9.0 out of 10, Wonderful, (2)
"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.
$314 nightly
The price is $333
Dec 10 - Dec 11
Total with taxes and fees
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Fridge, microwave, oven, stovetop
Updated 3BR Apartment in Westminster – Family Friendly

Apartment in Westminster

8.0 out of 10, Very Good, (5)
"The property was listed as capable of supporting up to 7 guests but the living room and dining area had seating for only four. Additionally, there was only one bathroom and the sleeping area for 5 guests was on a different floor. The HVAC system was not working well. The top floor was very warm while the lower level was very cold. However, the property is well located, with convenient access to restaurants and shopping."
United States
Jacob
$328 nightly
The price is $348
Dec 10 - Dec 11
Total with taxes and fees
Updated 3BR Apartment in Westminster – Family Friendly
Interior
New townhouse

Vacation Home in Frederick

9.4 out of 10, Exceptional, (9)
"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.
$340 nightly
The price is $361
Dec 15 - Dec 16
Total with taxes and fees
New townhouse
Exterior detail
Huge 1br apt, baby-friendly, dogs, walkable downtown

Apartment in Downtown Frederick

10.0 out of 10, Exceptional, (6)
$207 nightly
The price is $219
Jan 4 - Jan 5, 2026
Total with taxes and fees
Huge 1br apt, baby-friendly, dogs, walkable downtown
Fridge, microwave, oven, stovetop
Historic Bucher House with central location to Gettysburg and Lancaster Amish

Vacation Home in Hanover

9.8 out of 10, Exceptional, (68)
"The house is very nice. Fun walking around and exploring the history in the house. I now want to install a shuffleboard court at my own home!"
United States
Adam P.
$308 nightly
The price is $340
Dec 10 - Dec 11
Total with taxes and fees
Historic Bucher House with central location to Gettysburg and Lancaster Amish
Interior
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Vacation Home in Woodbine

$140 nightly
The price is $148
Dec 10 - Dec 11
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Interior
Cozy Peaceful Basement Cabin Vibes

Vacation Home in Ijamsville

10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
$341 nightly
The price is $361
Jan 3 - Jan 4, 2026
Total with taxes and fees
Cozy Peaceful Basement Cabin Vibes
Pool
Applewood Landing

Vacation Home in Gettysburg

10.0 out of 10, Exceptional, (6)
"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
$809 nightly
The price is $858
Dec 10 - Dec 11
Total with taxes and fees
Applewood Landing
Fridge, microwave, oven, stovetop
Experience Elevated Comfort: Luxe Breeze Townhouse.

Vacation Home in Owings Mills

9.6 out of 10, Exceptional, (4)
"Awesome stay and great location. Very quiet neighborhood, made the stay comfortable and relaxing. Very spacious and modern. "
United States
Jesse H.
$491 nightly
The price is $567
Jan 5 - Jan 6, 2026
Total with taxes and fees
Experience Elevated Comfort: Luxe Breeze Townhouse.
Private kitchen
Private, Peaceful Basement Apartment in a Serene Setting

Apartment in Sykesville

2.0 star property
$170 nightly
The price is $180
Dec 10 - Dec 11
Total with taxes and fees
Private, Peaceful Basement Apartment in a Serene Setting
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

Home2 Suites by Hilton Owings Mills

Home2 Suites by Hilton Owings Mills

10/10 Excellent
"We had 5 rooms for our group, and not a single complaint. The staff was friendly and helpful. Rooms were clean, spacious, and comfortable. We definitely plan to stay here the next time we are in the area."
Todd 3-night trip
Posted 9 hours ago
Home2 Suites by Hilton Owings Mills

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 $138 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?

Historic Bucher House with central location to Gettysburg and Lancaster Amish: Visitors like this New Windsor vacation home rental. It is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease 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. Make the most of the selection of games in this rental home to help you unwind.

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 Elk Run Vineyards.

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.