New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for New Windsor vacation rentals

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 2 - Jun 3
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
TV

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.0 out of 10, Wonderful, (4 reviews)
"Great location in downtown Hanover within walking distance of the square where there are various shops and dining options. "
United States
Danna W.
$257 nightly
The price is $284
Jun 7 - Jun 8
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
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.
$191 nightly
The price is $203
Jun 10 - Jun 11
Total with taxes and fees
Pet-friendly, heart of downtown

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, (127 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
$248 nightly
The price is $263
Jun 1 - Jun 2
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (90 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
$305 nightly
The price is $323
Jun 8 - Jun 9
Total with taxes and fees
Luxury Condo In Downtown Frederick
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (17 reviews)
"The house was spotless, and exactly where we needed/wanted to be. It was close to everything we wanted to see and we definitely will use it again!"
United States
Janet L.
$324 nightly
The price is $344
Jun 21 - Jun 22
Total with taxes and fees
Chic, pets, walk to downtown
Towels, toilet paper

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.4 out of 10, Exceptional, (8 reviews)
"This place was great. Ceiling is low, less that 6 feet in some spots. Location is great for visiting downtown Hanover. Parking was convenient. Stayed overnight with a buddy. Brought an air mattress so we didn’t have to share a bed (couch would’ve been a little small for sleeping comfortably)."
United States
Tim
$134 nightly
The price is $148
Jun 1 - Jun 2
Total with taxes and fees
Cozy studio charming Hanover
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.
$279 nightly
The price is $296
Jun 7 - Jun 8
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, oven, stovetop

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (93 reviews)
"Very clean and good location. "
United States
Kerry H.
$282 nightly
The price is $299
Jun 8 - Jun 9
Total with taxes and fees
Modern Condo Right off Market Street
1 bedroom, iron/ironing board, WiFi, bed sheets

Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
$115 nightly
The price is $132
Jun 1 - Jun 2
Total with taxes and fees
Newly Renovated Cozy Basement w/Private Entrance
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 4 - Jun 5
Total with taxes and fees
Cozy Pine Tree Nest
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (29 reviews)
"Great location, clean place. "
United States
Warren B.
$208 nightly
The price is $221
Jun 9 - Jun 10
Total with taxes and fees
Cozy, dog-friendly, 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 1 - Jun 2
Total with taxes and fees
Cozy Guesthouse in Woodstock, MD
Game 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
$140 nightly
The price is $148
Jun 2 - Jun 3
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
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, (9 reviews)
"Great little place for a weekend stay. Close to everything."
United States
Kurt S.
$247 nightly
The price is $262
Jun 15 - Jun 16
Total with taxes and fees
Huge 1br apt, baby-friendly, dogs, walkable 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)
"Immaculate apartment conveniently located close to Frederick Health Hospital in a quiet residential neighborhood. Just a fifteen minute walk to the heart of Frederick for memorable dining, interesting shops, and cozy cafés."
United States
Mark L.
$237 nightly
The price is $251
Jun 1 - Jun 2
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.4 out of 10, Exceptional, (3 reviews)
"Check-in was super easy. Communication with the owners was quick and easy. There was one hiccup that came up and were very quick to resolve. The house itself is a great historic home. They have done a great job modernizing it. My only feedback would be to have more supplies in the kitchen to accommodate preparing foods like knives, cutting boards, trays, etc. But otherwise, very happy with our stay and the beautiful property, and it being dog friendly!"
United States
Rachel W.
$411 nightly
The price is $434
Jun 1 - Jun 2
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
Fridge, microwave, oven, stovetop

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (15 reviews)
"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.
$443 nightly
The price is $470
Jun 1 - Jun 2
Total with taxes and fees
Newly constructed 6 bedroom home
Fridge, microwave, oven, stovetop

Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays

Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays
Westminster
8.4 out of 10, Very Good, (6 reviews)
"We enjoyed our stay, spacious rooms and cute decor. "
United States
Anonymous traveler
$305 nightly
The price is $336
Jun 30 - Jul 1
Total with taxes and fees
Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays
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

Best Western Historic Frederick

Best Western Historic Frederick

6/10 Okay
"It was a decent hotel"
ELainia 2-night trip
Posted less than an hour ago
Best Western Historic Frederick

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.

Explore a world of travel with Expedia

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?

Rural & Historic Detour Escape w/ Horses On-Site!: You might want to consider this vacation home rental near New Windsor, which offers a patio, a selection of books, and air-conditioning 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 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 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.