New Windsor Holiday Rentals

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Check prices for these dates

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in New Windsor

Fridge, microwave, oven, stovetop
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)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
The price is HK$771
HK$1,909 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

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.
The price is HK$897
HK$2,023 total
includes taxes & fees
7 Dec - 8 Dec
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop
*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*

Downtown Frederick
9.4 out of 10, Exceptional, (74)
"Enjoyed the hot tub with a view!"
United States
Matthew M.
The price is HK$817
HK$2,071 total
includes taxes & fees
7 Dec - 8 Dec
*Modern Condo In Downtown Frederick*
Smart TV
*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*

Downtown Frederick
9.0 out of 10, Wonderful, (70)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is HK$794
HK$2,013 total
includes taxes & fees
4 Jan - 5 Jan 2026
*Luxury Condo In Downtown Frederick*
Fridge, microwave, coffee/tea maker, electric kettle
Cozy Pine Tree Nest

Cozy Pine Tree Nest

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.
The price is HK$623
HK$1,321 total
includes taxes & fees
15 Dec - 16 Dec
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, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is HK$666
HK$1,077 total
includes taxes & fees
14 Dec - 15 Dec
Birch Cabin at Hunting Creek Hideaway
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, (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.
The price is HK$1,090
HK$2,442 total
includes taxes & fees
7 Dec - 8 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Fridge, microwave, oven, stovetop
Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown

Frederick
10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
The price is HK$490
HK$1,535 total
includes taxes & fees
8 Dec - 9 Dec
Cozy, dog-friendly, downtown
Smart TV
Pet-friendly, heart of downtown

Pet-friendly, heart of downtown

Frederick
10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is HK$462
HK$1,497 total
includes taxes & fees
10 Dec - 11 Dec
Pet-friendly, heart of downtown
Fridge, microwave, oven, stovetop
NEW! 9 Minute Walk To Carroll Creek - Bright Cozy Condo With Gallery Entrance.

NEW! 9 Minute Walk To Carroll Creek - Bright Cozy Condo With Gallery Entrance.

Frederick
10.0 out of 10, Exceptional, (2)
"The property was clean. I felt comfortable there. Nice community. The host communicated well. No complaints "
United States
Charles S.
The price is HK$849
HK$2,162 total
includes taxes & fees
9 Dec - 10 Dec
NEW! 9 Minute Walk To Carroll Creek - Bright Cozy Condo With Gallery Entrance.
Outdoor spa tub
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown

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

Westminster
8.0 out of 10, Very good, (1)
"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$981
HK$2,607 total
includes taxes & fees
7 Dec - 8 Dec
Green Street Oasis Hot Tub, Fire Pit & Walk to Downtown
Fridge, microwave, oven, stovetop
Historic Bucher House with central location to Gettysburg and Lancaster Amish

Historic Bucher House with central location to Gettysburg and Lancaster Amish

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.
The price is HK$2,095
HK$2,631 total
includes taxes & fees
7 Dec - 8 Dec
Historic Bucher House with central location to Gettysburg and Lancaster Amish
Property grounds
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, (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.
The price is HK$771
HK$1,947 total
includes taxes & fees
9 Dec - 10 Dec
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Private kitchen
Private, Peaceful Basement Apartment in a Serene Setting

Private, Peaceful Basement Apartment in a Serene Setting

2.0 star property
Sykesville
The price is HK$934
HK$1,403 total
includes taxes & fees
17 Dec - 18 Dec
Private, Peaceful Basement Apartment in a Serene Setting
Fridge, microwave, oven, stovetop
Updated 3BR Apartment in Westminster – Family Friendly

Updated 3BR Apartment in Westminster – Family Friendly

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
The price is HK$946
HK$2,422 total
includes taxes & fees
5 Dec - 6 Dec
Updated 3BR Apartment in Westminster – Family Friendly
Pool
Applewood Landing

Applewood Landing

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 traveller
The price is HK$1,393
HK$6,684 total
includes taxes & fees
9 Dec - 10 Dec
Applewood Landing
Interior
New townhouse

New townhouse

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.
The price is HK$1,177
HK$2,807 total
includes taxes & fees
16 Dec - 17 Dec
New townhouse
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)
The price is HK$724
HK$1,799 total
includes taxes & fees
4 Jan - 5 Jan 2026
Huge 1br apt, baby-friendly, dogs, walkable downtown
Fridge, microwave, oven, stovetop
Newly constructed 6 bedroom home

Newly constructed 6 bedroom home

Frederick
10.0 out of 10, Exceptional, (14)
"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 HK$1,658
HK$3,614 total
includes taxes & fees
16 Dec - 17 Dec
Newly constructed 6 bedroom home
Interior
Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes

Ijamsville
10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
The price is HK$1,946
HK$2,813 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Peaceful Basement Cabin Vibes
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

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

10/10 Excellent
"Staff very courteous "
barbara 2-night trip
Posted 2 days ago
Hyatt Place Baltimore/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:

  • View our selection of featured holiday rentals in New Windsor
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

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?

Historic Bucher House with central location to Gettysburg and Lancaster Amish: This holiday home rental outside of New Windsor is located in the city centre, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most 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 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.