Default HTG hotel image

New Windsor Vacation Rentals

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for New Windsor vacation rentals

A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 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.
$412 nightly
The price is $437
Sep 11 - Sep 12
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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
Sep 11 - Sep 12
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
A ping pong table in a room with a television, a plant, and a sofa.

3. 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.
$130 nightly
The price is $138
Sep 11 - Sep 12
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

4. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
$199 nightly
The price is $211
Sep 14 - Sep 15
Total with taxes and fees
Cozy, dog-friendly, downtown
A modern apartment with a living room, kitchen, and dining area.

5. 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.
$199 nightly
The price is $211
Sep 14 - Sep 15
Total with taxes and fees
Pet-friendly, heart of downtown
A wooden deck with a fire pit, outdoor furniture, and string lights.

6. Green Street Oasis – Walk to Downtown Westminster & McDaniel College

Green Street Oasis – Walk to Downtown Westminster & McDaniel College
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.
$443 nightly
The price is $469
Sep 13 - Sep 14
Total with taxes and fees
Green Street Oasis – Walk to Downtown Westminster & McDaniel College
A kitchen with two stainless steel sinks, a window with a plant, and a white door.

7. 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, (17 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
$203 nightly
The price is $215
Sep 13 - Sep 14
Total with taxes and fees
Patty's Place - Private and Convenient Apartment near Downtown
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

8. 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
Sep 28 - Sep 29
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

9. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (13 reviews)
"Place was as described. "
United States
Katie F.
$134 nightly
The price is $148
Sep 14 - Sep 15
Total with taxes and fees
Cozy studio charming Hanover
A living room with a large mirror, a sofa with cushions, a television, and decorative items on a wooden console.

10. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
$265 nightly
The price is $281
Sep 14 - Sep 15
Total with taxes and fees
Downtown Frederick retreat with parking. Dog- and baby-friendly!
A modern hotel room with a large bed, two bedside tables, a flat-screen TV, a seating area with a chair and a small table, and a decorative plant.

11. Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay for the night."
United States
Sheila K.
$150 nightly
The price is $173
Sep 13 - Sep 14
Total with taxes and fees
Newly Renovated Cozy Basement w/Private Entrance
A park with a pond, a bridge, and a church in the background.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (137 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
$256 nightly
The price is $271
Sep 13 - Sep 14
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

13. 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.
$246 nightly
The price is $260
Sep 22 - Sep 23
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

14. 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, (52 reviews)
"Great lodging and communicative host"
United States
Peggy D.
$257 nightly
The price is $272
Sep 16 - Sep 17
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

15. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (1 review)
"Great stay in downtown Frederick with good amenities especially with the W/D for an extended trip like i did for my work travel. Hosts are responsive and helpful. Would definitely book again on a return trip."
United States
Dave T.
$232 nightly
The price is $246
Sep 22 - Sep 23
Total with taxes and fees
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

16. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (4 reviews)
"The property is excellent! Beautiful and peaceful surroundings. It was clean warm and welcoming. It’s pet friendly though we didn’t travel with pets. Outstanding host!"
United States
David M.
$379 nightly
The price is $401
Sep 15 - Sep 16
Total with taxes and fees
Private Sauna, Fireplace and Country Views
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

17. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Great place!"
United States
Danielle G.
$314 nightly
The price is $333
Sep 15 - Sep 16
Total with taxes and fees
Modern Condo Right off Market Street
A living room with a flat-screen TV on a wooden TV stand, a fireplace with a mantel, and a patterned rug on the floor.

18. Downtown Loft on Market Street-Great Location

Downtown Loft on Market Street-Great Location
Downtown Frederick
$113 nightly
The price is $120
Sep 29 - Sep 30
Total with taxes and fees
Downtown Loft on Market Street-Great Location
A modern kitchen with grey cabinets, a central island, and pendant lighting.

19. 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.
$327 nightly
The price is $347
Sep 23 - Sep 24
Total with taxes and fees
Luxury Condo In Downtown Frederick
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

20. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (21 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
$456 nightly
The price is $483
Sep 27 - Sep 28
Total with taxes and fees
Newly constructed 6 bedroom home
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

Eisenhower Hotel & Conference Center

Eisenhower Hotel & Conference Center

10/10 Excellent
"Everything was great!"
amber 2-night trip
Posted 14 hours ago
Eisenhower Hotel & Conference Center

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 $271 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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: Visitors like this New Windsor vacation home rental. It is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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 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.