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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for New Windsor vacation rentals

Property grounds

1. Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat

Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
Westminster
8.0 out of 10, Very Good, (7 reviews)
"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.
$503 nightly
The price is $533
Aug 20 - Aug 21
Total with taxes and fees
Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
House (3 Bedrooms) | Interior

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
$408 nightly
The price is $432
Aug 9 - Aug 10
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.6 out of 10, Exceptional, (5 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.
$412 nightly
The price is $437
Aug 9 - Aug 10
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
Interior

4. The Gathering Place Luxury Sauna Retreat

The Gathering Place Luxury Sauna Retreat
Mount Airy
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful location with a beautiful field where wild animals visited. Hosts really took care of the amenities (great coffee bar). Close to Mt Airy and vineyards."
United States
Richard B.
$416 nightly
The price is $441
Sep 1 - Sep 2
Total with taxes and fees
The Gathering Place Luxury Sauna Retreat
TV

5. 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)
"Great location in downtown Hanover within walking distance of the square where there are various shops and dining options. "
United States
Danna W.
$244 nightly
The price is $269
Aug 11 - Aug 12
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Dining

6. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
$333 nightly
The price is $353
Aug 17 - Aug 18
Total with taxes and fees
Luxury Condo In Downtown Frederick
A park with a pond, a bridge, and a church in the background.

7. 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, (133 reviews)
"The place was so fun and close to the bars! The rooms where cleans "
United States
Anonymous traveler
$273 nightly
The price is $289
Aug 9 - Aug 10
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Coffee/tea maker, fridge, microwave, oven

8. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (101 reviews)
"Great place to stay. It was close to the park. It is a beautiful clean place. "
United States
Kimberly & Randy H.
$317 nightly
The price is $336
Aug 17 - Aug 18
Total with taxes and fees
Modern Condo Right off Market Street
Coffee/tea maker, fridge, microwave, oven

9. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (69 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
$251 nightly
The price is $266
Aug 12 - Aug 13
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Smart TV

10. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (12 reviews)
"Place was as described. "
United States
Katie F.
$134 nightly
The price is $148
Aug 9 - Aug 10
Total with taxes and fees
Cozy studio charming Hanover
1 bedroom, WiFi (free), bed sheets

11. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (35 reviews)
"Great location, clean place. "
United States
Warren B.
$189 nightly
The price is $200
Aug 10 - Aug 11
Total with taxes and fees
Cozy, dog-friendly, downtown
Exterior

12. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
$525 nightly
The price is $557
Aug 25 - Aug 26
Total with taxes and fees
New townhouse
Outdoor dining

13. 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, (51 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
$256 nightly
The price is $271
Aug 31 - Sep 1
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Smart TV, books

14. Cozy Peaceful Basement Cabin Vibes

Cozy Peaceful Basement Cabin Vibes
Ijamsville
10.0 out of 10, Exceptional, (5 reviews)
"Good trip."
United States
Jewell F.
$314 nightly
The price is $333
Aug 22 - Aug 23
Total with taxes and fees
Cozy Peaceful Basement Cabin Vibes
Game room

15. 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
8.0 out of 10, Very Good, (2 reviews)
"The stay was at a beautiful new home. Great host. Location close to Interstate 70. I had everything I needed. Took in the sights in DC via the Greenline Metro. I would definitely stay here again."
United States
Scott C.
$161 nightly
The price is $171
Sep 6 - Sep 7
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
Coffee/tea maker, fridge, microwave, oven

16. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (19 reviews)
"Everything was excellent "
United States
Ronald G.
$472 nightly
The price is $500
Aug 11 - Aug 12
Total with taxes and fees
Newly constructed 6 bedroom home
Coffee/tea maker, fridge, microwave, toaster

17. Patty's Place - Private and Convenient Apartment near Downtown

Patty's Place - Private and Convenient Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (15 reviews)
"I’m a little sad to go I had the best stay. So comfortable so quiet, great stay. I will definitely be back "
United States
Anonymous traveler
$202 nightly
The price is $214
Aug 11 - Aug 12
Total with taxes and fees
Patty's Place - Private and Convenient Apartment near Downtown
Smart TV

18. 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 $202
Aug 31 - Sep 1
Total with taxes and fees
Pet-friendly, heart of downtown
Microwave, stovetop, dishwasher

19. The blissful house in Howard County with 3 bedrooms 3 bathrooms.

The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Marriottsville
8.8 out of 10, Excellent, (6 reviews)
"Great communication with host, perfect location for where we needed to be, house is very clean and spacious!"
United States
Ruth M.
$774 nightly
The price is $820
Aug 11 - Aug 12
Total with taxes and fees
The blissful house in Howard County with 3 bedrooms 3 bathrooms.
Interior

20. 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
Sep 1 - Sep 2
Total with taxes and fees
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
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

Inn at Cemetery Hill

Inn at Cemetery Hill

10/10 Excellent
"Great location"
Stacey 3-night trip
Posted 1 hour ago
Inn at Cemetery Hill

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?

Elegant Escape w/ Premium Comfort & Free Parking: Visitors like this New Windsor vacation home rental. It is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. 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 Union Mills Homestead 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.