New Windsor Vacation Rentals

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Vacation Rentals in New Windsor

Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (61)
"Beautiful views from the wrap around porch. Comfortable inside including the bed. Lots of neat things to look at. Highly recommend!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Cottage, 2 Bedrooms (Loft, No Pets)
Round Top Campground
2.0 star property
9.2 out of 10, Wonderful, (10)
"The area was beautiful and very quite! We loved the cabin we stayed in. While we did run into some minor issues, staff was VERY accommodating and attentive. We hope to come back and would love to stay on the grounds again. They love dogs and that made us feel more comfortable. The pool was awesome, as was the arcade room for our younger members of the group! "
The price is CA $288
CA $320 total
includes taxes & fees
Jun 2 - Jun 3
Round Top Campground
Interior
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, (17)
"We had previously visited Frederick last November and had only been able to spend a little bit of our visit in Historic Frederick. We loved staying in historic Frederick and the property was unique, very clean and well laid out. I should have realized was that 'penthouse' in a historic home would mean steps. I am blind in one eye and have poor physical balance so carrying luggage up stairs is challenging. Nonetheless, we loved the layout and amenities of the property. The view from the deck was...
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
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Fridge, microwave, oven, stovetop
Escape to the mountains! Beat the Summer heat!
10.0 out of 10, Exceptional, (261)
"We unfortunately did not utilize all this home had to offer due to being gone most of the time during our stay. We loved the smell of the wood when you walked in and it was plenty of space for all of us. We will definitely book this home if we visit the area again. ."
Escape to the mountains! Beat the Summer heat!
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.4 out of 10, Exceptional, (96)
"A perfect location in Frederick. The Carroll Creek Canal is right behind the house and is beautifull! Aaron gave us excellent recommendations as to where to visit and eat. The house is older but clean, tidy and comfortable. We did use the kitchen to cook and gave Aaron a few pointers to improve what he had for utensils. Overall, I would come back again. Thanks Aaron"
The price is CA $191
CA $429 total
includes taxes & fees
Jun 2 - Jun 3
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Cookware/dishes/utensils
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
9.0 out of 10, Wonderful, (2)
"Lovely well kept property. It has everything you need. Comfortable beds and convenient location. The only drawback is the front bedroom has LOTS of street noise. I used a fan for white noise and earplugs. It’s on a busy street. Fire Station is nearby too. Great park for kids across the street. Close to a few great restaurants within walking distance."
Cozy Maryland Abode - Gas Grill, Near Devil’s Den!
Fridge, microwave, stovetop, dishwasher
Farmhouse on River, 12 Miles to Liberty Mountain
9.6 out of 10, Exceptional, (35)
"We loved being all together and the house allowed for us to do that. Check in was easy. Location was great-nice off the main road but close to towns. Historic home so we expect the tiny door into the small room. We expect the themed rooms to compliment the hunter theme. Huge turkey was a turn off above the bed. We did not appreciate the dust all around, old beds, and stains on bedding. Kitchen pots and pans need updating. We ordered out food for most of our meals. Never heard back from with host...
Farmhouse on River, 12 Miles to Liberty Mountain
Fridge, microwave, oven, stovetop
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
10.0 out of 10, Exceptional, (46)
"Great little place to stay in Frederick for a couple or small family. House was clean and up to date with good Wi-Fi and well set up kitchen. Best part was being able to walk into the center of town for shops and restaurants in 5 minutes! Highly recommended!!"
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
Fridge, microwave, oven, stovetop
The GRACE Villa - a homey affair!
10.0 out of 10, Exceptional, (4)
"VERY NICE PROPERTY"
The GRACE Villa - a homey affair!
Property grounds
Farmhouse Getaway with fresh eggs and vegetables (In Season)
8.6 out of 10, Excellent, (10)
"Quiet peaceful location with nice country setting,"
The price is CA $232
CA $327 total
includes taxes & fees
May 27 - May 28
Farmhouse Getaway with fresh eggs and vegetables (In Season)
View from property
1850 Historic Log Cabin
9.4 out of 10, Exceptional, (27)
"Linda was a wonderful host. She treated us like family. The cabin so also very inviting as soon as you came through the door. Would definitely stay there again"
1850 Historic Log Cabin
Living area
The Madison
10.0 out of 10, Exceptional, (14)
"The floor plan and furnishings were fantastic. Very comfortable and inviting. Superb."
The Madison
Fridge, microwave, oven, stovetop
Peaceful Hollow | 4 Bed, 2 Bath
10.0 out of 10, Exceptional, (23)
"Such a wonderful place that this is my second this year and hop to come back in the fall."
Peaceful Hollow | 4 Bed, 2 Bath
Exterior
Quiet Apartment in Coolest Small Town in America!
9.4 out of 10, Exceptional, (32)
"Very nice apartment and great location. Apartment is well appointed for a long or short stay, with everything needed for comfort, including a small desk for working (this was a "working" trip). With family in the area, we will be back and this is a perfect spot for a getaway. Very clean and quiet."
Quiet Apartment in Coolest Small Town in America!
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (22)
"Very roomy, comfortable, quiet. Great location"
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, stovetop, dishwasher
Stylish + Serene West Friendship Hidden Gem!
9.0 out of 10, Wonderful, (10)
"The house was nice. We stayed for work. Will stay again."
Stylish + Serene West Friendship Hidden Gem!
Smart TV
*Luxury Condo In Downtown Frederick*
9.6 out of 10, Exceptional, (41)
"Very historic town great property walking distance to everything"
The price is CA $273
CA $487 total
includes taxes & fees
May 28 - May 29
*Luxury Condo In Downtown Frederick*
Fridge, microwave, oven, stovetop
CASA BLANCA
10.0 out of 10, Exceptional, (2)
"Really enjoyed the space. We were multiple families of a girl's club lacrosse team from out of state. The kitchen was large, and we used the grill outside for dinner. The girls had room to hang out together in the loft. We thought we would use the pool, but in the end, we didn't. Nice to have it, just in case. There are restaurants and grocery stores nearby in Eldersburg or Owings Mills. We would definitely stay again."
CASA BLANCA
Exterior
“The Train Depot” 2nd oldest in the US
10.0 out of 10, Exceptional, (61)
"We enjoyed our weekend in Frederick and LOVED the property we stayed in! Everything was as shown in the listing and it was even better in person. The owner thought of everything to make the stay great and was quick to respond when I asked a question."
“The Train Depot” 2nd oldest in the US
Fridge, microwave, oven, stovetop
Gorgeous 1840 Log Cabin- Downtown
10.0 out of 10, Exceptional, (110)
"My company, Mettle Events, Inc. are the timers for the Frederick Running Festival, and we like to stay in rentals vs. hotels. The Cabin was perfect! Clean, off-street parking, walkable location to restaurants & breweries, five minutes to our job site (the fairgrounds) and I loved that everything was labeled! the house rules were clear and easy to understand, and the price was right! We will definitely be returning to The Cabin!"
Gorgeous 1840 Log Cabin- Downtown
Don't see what you're looking for?
See all available properties in New Windsor
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.

Other types of properties in New Windsor you may be interested in

Room, 2 Queen Beds, Non Smoking
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1008)
"Nice and clean. Very good quality-price ratio."
The price is CA $111
CA $123 total
includes taxes & fees
Jun 16 - Jun 17
Country Inn & Suites by Radisson, Frederick, MD
Exterior
Hyatt Place Baltimore/Owings Mills
3.0 star property
8.2 out of 10, Very good, (1005)
"We stayed overnight for a family event. The room was nice and spacious. The surrounding area was ok. The hotel workers were nice and helpful."
The price is CA $167
CA $193 total
includes taxes & fees
Jun 2 - Jun 3
Hyatt Place Baltimore/Owings Mills
Exterior
Hilton Garden Inn Frederick
3.0 star property
9.0 out of 10, Wonderful, (1002)
"The check-in service was excellent! unfortunately, there was a problem. The hotel had a main water pipe burst at 3:45am. that resulted in the entire hotel being evacuated. I do want to say the check-in clerk was exceptional in handling this situation. He assured us the hotel would give us a refund if we called Expedia. I was given the info. that Expedia needed to process the refund and it appears that this will be taken care of. Thank-you so much and thank-you (check-in clerk) Art."
The price is CA $138
CA $153 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Garden Inn Frederick
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with New Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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’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 larger area, you’ll find Old Westminster Winery and McDaniel College.

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.

Recent reviews of New Windsor properties
Expedia verified reviews