Default HTG hotel image

New Windsor Vacation Rentals

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for New Windsor vacation rentals

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, (68 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
$324 nightly
The price is $343
Jul 21 - Jul 22
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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, (6 reviews)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
$255 nightly
The price is $282
Jun 24 - Jun 25
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Interior

Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
$407 nightly
The price is $432
Jun 25 - Jun 26
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
Microwave, oven, stovetop, dishwasher

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
$485 nightly
The price is $548
Jun 24 - Jun 25
Total with taxes and fees
Secret' Desires-Adult Only
Fridge, microwave, oven, stovetop

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (96 reviews)
"Lovely, cozy apartment, more spacious than we imagined and the perfect place to retreat to after the bustling shops and restaurants a few blocks away."
United States
Alexandra W.
$271 nightly
The price is $287
Jun 24 - Jun 25
Total with taxes and fees
Modern Condo Right off Market Street
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres

Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres
Westminster
$369 nightly
The price is $391
Jul 1 - Jul 2
Total with taxes and fees
Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres
Smart TV

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
$206 nightly
The price is $218
Jul 7 - Jul 8
Total with taxes and fees
Pet-friendly, heart of downtown
Property grounds

Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD
Woodstock
2.0 out of 10, (1 review)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
United States
Marie E M.
$199 nightly
The price is $230
Jun 24 - Jun 25
Total with taxes and fees
Cozy Guesthouse in Woodstock, MD
Interior

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

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (51 reviews)
"Everything was great!"
United States
Corey G.
$569 nightly
The price is $628
Jun 24 - Jun 25
Total with taxes and fees
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (94 reviews)
"All amenities were top notch "
United States
John M.
$318 nightly
The price is $337
Jun 30 - Jul 1
Total with taxes and fees
Luxury Condo In Downtown Frederick
Fridge, microwave, oven, stovetop

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (18 reviews)
"Everything was excellent "
United States
Ronald G.
$440 nightly
The price is $466
Jun 24 - Jun 25
Total with taxes and fees
Newly constructed 6 bedroom home

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, (129 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
$262 nightly
The price is $278
Jul 6 - Jul 7
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
TV, foosball, 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.
$160 nightly
The price is $170
Jun 29 - Jun 30
Total with taxes and fees
Cozy Pine Tree Nest
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (18 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
$266 nightly
The price is $282
Jul 1 - Jul 2
Total with taxes and fees
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, (44 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
$238 nightly
The price is $252
Jul 6 - Jul 7
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Exterior

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (10 reviews)
"This stay was flawless and did not disappoint. The home was better than advertised and check in was painless. Would stay there again without hesitation!"
United States
Jeremy G.
$482 nightly
The price is $511
Jun 30 - Jul 1
Total with taxes and fees
New townhouse
Towels, toilet paper

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
8.6 out of 10, Excellent, (10 reviews)
"I stayed for a week while in town for work. Everything was very clean and the space was exactly what I needed. I believe I saw on another review about the gradual drop in the ceiling as you move from the kitchen into the living room so that is the only thing to watch out for. I’m 6’1 and managed it just fine. Would stay again! "
United States
Jonathan M.
$134 nightly
The price is $148
Jun 25 - Jun 26
Total with taxes and fees
Cozy studio charming Hanover
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (32 reviews)
"Great location, clean place. "
United States
Warren B.
$213 nightly
The price is $226
Jul 20 - Jul 21
Total with taxes and fees
Cozy, dog-friendly, downtown
Exterior

Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking

Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking
Garrison
9.0 out of 10, Wonderful, (2 reviews)
"The host was very responsive to questions prior to our arrival, as well as a few things during our stay. Was a great place for my family to stay with our two dogs, as well as plenty of room for local family to come for dinner and catch up. Great location with plenty of shops and food choices near by, as well as groceries stores to get stuff for the house. Would definitely stay here again if needed to."
United States
Carly L.
$505 nightly
The price is $583
Jun 24 - Jun 25
Total with taxes and fees
Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking
Interior

Rural & Historic Detour Escape w/ Horses On-Site!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.6 out of 10, Exceptional, (4 reviews)
"We had a great time. It is an older house but wonderful. It is in the country with lots of green fields surrounding it. The porch with the rockers was my favorite place to be when we weren’t site seeing, It was so peaceful. I would definitely stay here again."
United States
Charla H.
$417 nightly
The price is $441
Jun 25 - Jun 26
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
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

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

10/10 Excellent
"Everything was wonderful. I had an amazing time."
Alice 2-night trip
Posted 3 hours ago
Hyatt Place Baltimore/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 $148 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.

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?

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome
: You might want to consider this vacation home rental near New Windsor, which is located in the city center and has a patio, a garden, and air-conditioning 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Winchester Park. In the larger area, you’ll find Old Westminster Winery and Carroll County Farm Museum.

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.