Holiday Rentals in New Windsor

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Holiday Rentals in New Windsor

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Exterior

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (88)
"Cozy cabin, wonderful hosts, great location near the AT. Probably the most thoughtful host we’ve had, they’ve thought of everything from breakfast treats and extra linens, even dog treats."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Miscellaneous

A newly renovated, pet-friendly Penthouse condo with private rooftop deck.

9.6 out of 10, Exceptional, (36)
"The property was lovely. Just as pictured. The host was very responsive throughout the booking, and check-in process. As others have mentioned, the intersection can be a bit busy, and noisy in the morning. The temp outside was in the 20 degree range, and the heat and hot water inside never got exceptionally warm. "
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
*Luxury Condo In Downtown Frederick*
Smart TV

*Luxury Condo In Downtown Frederick*

9.4 out of 10, Exceptional, (49)
"Very comfortable stay - lovely finishes in bathrooms and kitchen."
The price is €236
includes taxes & fees
3 Jan - 4 Jan 2025
*Luxury Condo In Downtown Frederick*
The GRACE Villa - a homey affair!
Interior

The GRACE Villa - a homey affair!

9.4 out of 10, Exceptional, (10)
"My family was in town for my son's funeral service. He, 23yrs old, was active duty army sgt who passed away while on deployment overseas. Grace Villa was the only 5 bedrm property large enough for 10 people to stay comfortably. The home was exactly as described in the listing, very clean. The house can sleep 15 guests easily but the kitchen was not equipped with adequate dishware, cookware, it lacked basic utensils required for cooking. That was challenging."
The GRACE Villa - a homey affair!
1850 Historic Log Cabin
Dining

1850 Historic Log Cabin

9.4 out of 10, Exceptional, (31)
"Linda is one of the most responsive hosts we work with. The home is full of character and clean. The bottle of wine is always a nice touch! We've stayed here twice and works book again!"
1850 Historic Log Cabin
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

9.4 out of 10, Exceptional, (104)
"We loved the historic home and its proximity to Carroll Creek and shopping! We were in town for a wedding and were able to walk everywhere we needed to go. "
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Gorgeous 1840 Log Cabin- Downtown
Fridge, microwave, oven, stovetop

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (122)
"I come to Frederick a lot and so have stayed at many of the VRBO properties. This property is the best property I have seen in Frederick in terms of comfort and aesthetic appeal. Everything was super nice and classy from the linens to the dishware. It is in an excellent location within a short walk to Market street and the canal. The host is really nice and very accommodating. I strongly recommend it especially if you want to be downtown."
Gorgeous 1840 Log Cabin- Downtown
Open Floor Plan, Spa Tub, Chef’s Kitchen, King Bed,
Fridge, microwave, oven, stovetop

Open Floor Plan, Spa Tub, Chef’s Kitchen, King Bed,

9.6 out of 10, Exceptional, (5)
"We have enjoyed this property each of the past two years for our family gathering. One of the best places we have stayed. Clean, spacious, well stocked and great communication with the owner. We will keep coming back"
The price is €471
includes taxes & fees
5 Jan - 6 Jan 2025
Open Floor Plan, Spa Tub, Chef’s Kitchen, King Bed,
Snow is coming! Only five minutes from Liberty Ski Resort.. Come stay with us!
Fridge, microwave, oven, stovetop

Snow is coming! Only five minutes from Liberty Ski Resort.. Come stay with us!

10.0 out of 10, Exceptional, (283)
"Our family of six enjoyed our stay in this cabin. We were very comfortable and found everything we needed in the cabin. The driveway was a little tight with our big vehicle, but manageable. Arriving in the daylight would have helped. Would definitely book again!"
Snow is coming! Only five minutes from Liberty Ski Resort.. Come stay with us!
Stylish + Serene West Friendship Hidden Gem!
Fridge, microwave, stovetop, dishwasher

Stylish + Serene West Friendship Hidden Gem!

9.0 out of 10, Wonderful, (14)
"Felt more remote than it is, which is just what we wanted. Spent lots of time in the gazebo. Odd design so that light shines into bedrooms from other rooms at ceiling, but slept great anyway. Well stocked and clean, very comfortable. We would return for another family get-together."
Stylish + Serene West Friendship Hidden Gem!
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
Dishwasher, cookware/dishes/utensils, paper towels, dining tables

Cozy Maryland Abode - Gas Grill, Near Devil’s Den!

9.2 out of 10, Wonderful, (7)
"We were here on business in Gettysburg but chose to stay here in Emmitsburg. So glad we did!"
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

10.0 out of 10, Exceptional, (30)
"This is a beautiful, tasteful, updated home. I was surprised at how comfortable the beds were! It's in a great location, and we appreciated the prompt and thoughtful host communication. It's very reasonably priced for all that you get with this stay! Parking was tricky for us as we rented on the night of street sweeping and had to park several blocks away. Other than that, this is an excellent place to stay. "
The price is €283
includes taxes & fees
7 Jan - 8 Jan 2025
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!
Interior

Peaceful Home w/ Patio < 2 Mi to Nat'l Park!

10.0 out of 10, Exceptional, (17)
"Everything was perfect, and comfortable. Owners really care about their visitors. Home was walk in perfect for a family long weekend. Happened to be Thurmont's annual colorfest festival, and home pefectly located, nestled away yet close enough for easy walking. Highly recommend. "
Peaceful Home w/ Patio < 2 Mi to Nat'l Park!
Arboretum Suite in the historic Manor House!
Terrace/patio

Arboretum Suite in the historic Manor House!

10.0 out of 10, Exceptional, (3)
"Very comfortable! "
Arboretum Suite in the historic Manor House!
Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC
Property grounds

Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC

10.0 out of 10, Exceptional, (34)
"Comfortable, Convenient, & Close (to local Frederick attractions/needs, etc.). 2nd stay & the hosts added some quality cookware (based on my 1st stay recommendations) which was much appreciated. Hoping to stay again & again whenever I’m in the area."
Charming 1 Bedroom Apt- Best Location Near Downtown Frederick & DC
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fridge, microwave, oven, stovetop

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (44)
"Stunning property and well-maintained. I only wish we had more time here! Eileen was incredibly accommodating and flexible with our check-in. "
The price is €618
includes taxes & fees
3 Jan - 4 Jan 2025
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Sunlight 2BR townhouse w/ free private parking in Downtown Frederick
Fridge, microwave, oven, stovetop

Sunlight 2BR townhouse w/ free private parking in Downtown Frederick

9.6 out of 10, Exceptional, (11)
"Very comfortable house with all amenities and essentials provided. Very comfortable beds. Shopping street right around the corner."
Sunlight 2BR townhouse w/ free private parking in Downtown Frederick
Frederick MD, Come Home to Style & Comfort, Carroll Creek, Brew, Arts, with OSP
Property grounds

Frederick MD, Come Home to Style & Comfort, Carroll Creek, Brew, Arts, with OSP

10.0 out of 10, Exceptional, (3)
"My wife and I were celebrating our anniversary. This place was perfect. The house was clean and very well appointed. It even has an extensive record collection. A great find. Thank you Laurie "
Frederick MD, Come Home to Style & Comfort, Carroll Creek, Brew, Arts, with OSP
Peaceful Hollow | 4 Bed, 2 Bath
Fridge, microwave, oven, stovetop

Peaceful Hollow | 4 Bed, 2 Bath

10.0 out of 10, Exceptional, (29)
"The house was beautiful. So secluded and quiet. The kitchen had everything. Very clean yard well kept. Very detailed in everything. Fire pit was great, wonderful screened porch to sit on at night. Outside games and seating and chairs for outside available. My daughter got married at Hummingbird Chateau. We rented the house for the family to stay in for the time we were there for the event. So convenient to everything. Loved it!"
Peaceful Hollow | 4 Bed, 2 Bath
Farmhouse on River, 12 Miles to Liberty Mountain
Fridge, microwave, stovetop, dishwasher

Farmhouse on River, 12 Miles to Liberty Mountain

9.8 out of 10, Exceptional, (43)
"Wonderful family homestead. The place is better than what the online pictures show, including how quiet it is outside of the home. FYI DO NOT TAKE THE CRUMMY ASPHALT ROAD! Google took me to a locked gate in a potato field at night lol. Strongly recommend and we will definitely be back next time we visit Gettysburg College."
Farmhouse on River, 12 Miles to Liberty Mountain
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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Other types of properties in New Windsor you may be interested in

Hyatt Place Baltimore/Owings Mills
Exterior

Hyatt Place Baltimore/Owings Mills

3.0 star property
8.2 out of 10, Very good, (1012)
"Older room. Property was clean and staff was friendly and attentive."
The price is €108
includes taxes & fees
30 Dec - 31 Dec
Hyatt Place Baltimore/Owings Mills
Country Inn & Suites by Radisson, Frederick, MD
Room, 2 Queen Beds, Non Smoking

Country Inn & Suites by Radisson, Frederick, MD

3.0 star property
8.4 out of 10, Very good, (1008)
"Nice place for overnight stay."
The price is €94
includes taxes & fees
5 Jan - 6 Jan 2025
Country Inn & Suites by Radisson, Frederick, MD
Hampton Inn & Suites Frederick-Fort Detrick
Exterior

Hampton Inn & Suites Frederick-Fort Detrick

2.5 star property
8.8 out of 10, Excellent, (1005)
"God servise "
The price is €108
includes taxes & fees
4 Jan - 5 Jan 2025
Hampton Inn & Suites Frederick-Fort Detrick
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.

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?

19th Century Mansion/Farm House: This holiday home rental outside of New Windsor offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 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 Carroll Creek Linear Park. In the wider area, you’ll find Old Westminster Winery and McDaniel College.

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.