New Windsor Holiday Rentals

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Check prices for these dates

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

Our top choices for New Windsor holiday 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.
The price is HK$464
HK$1,485 total
includes taxes & fees
4 Feb - 5 Feb
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
The price is HK$436
HK$1,456 total
includes taxes & fees
5 Feb - 6 Feb
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.
The price is HK$409
HK$1,510 total
includes taxes & fees
5 Feb - 6 Feb
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
TV, table football, 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.
The price is HK$626
HK$1,326 total
includes taxes & fees
5 Feb - 6 Feb
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.
The price is HK$760
HK$1,178 total
includes taxes & fees
4 Feb - 5 Feb
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.
The price is HK$930
HK$2,045 total
includes taxes & fees
17 Feb - 18 Feb
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.
The price is HK$773
HK$1,954 total
includes taxes & fees
4 Feb - 5 Feb
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Pool

Applewood Landing

Applewood Landing
Gettysburg
10.0 out of 10, Exceptional, (9 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 HK$1,195
HK$6,392 total
includes taxes & fees
4 Feb - 5 Feb
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.
The price is HK$820
HK$2,053 total
includes taxes & fees
4 Feb - 5 Feb
*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, (6 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.
The price is HK$586
HK$1,648 total
includes taxes & fees
10 Feb - 11 Feb
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
The price is HK$976
HK$2,216 total
includes taxes & fees
6 Feb - 7 Feb
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
The price is HK$797
HK$2,028 total
includes taxes & fees
5 Feb - 6 Feb
*Luxury Condo In Downtown Frederick*
Living area

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
The price is HK$773
HK$1,024 total
includes taxes & fees
4 Feb - 5 Feb
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.
The price is HK$1,033
HK$2,677 total
includes taxes & fees
8 Feb - 9 Feb
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.
The price is HK$944
HK$2,251 total
includes taxes & fees
4 Feb - 5 Feb
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.
The price is HK$1,953
HK$3,207 total
includes taxes & fees
1 Mar - 2 Mar
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.
The price is HK$1,212
HK$2,469 total
includes taxes & fees
4 Feb - 5 Feb
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.
The price is HK$4,647
HK$6,814 total
includes taxes & fees
8 Feb - 9 Feb
The blissful house in Howard County with 3 bedrooms 3 bathrooms.

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.
The price is HK$1,234
HK$2,608 total
includes taxes & fees
9 Feb - 10 Feb
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Games 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
The price is HK$844
HK$1,225 total
includes taxes & fees
4 Feb - 5 Feb
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.
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Top New Windsor Hotel Reviews

Home2 Suites by Hilton Owings Mills

Home2 Suites by Hilton Owings Mills

10/10 Excellent
"The room was a great space, breakfast was good, there was a good bit of variety for food "
yvonne 1-night trip
Posted 2 days ago
Home2 Suites by Hilton Owings Mills

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in New Windsor!

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?

*Luxury Condo In Downtown Frederick*: This holiday home rental outside of New Windsor is located in the city centre, 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 that 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 wider area, you’ll find Old Westminster Winery and Carroll County Farm Museum.

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.