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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for New Windsor vacation rentals

A wooden deck with a fire pit, outdoor furniture, and string lights.

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

Green Street Oasis – Walk to Downtown Westminster & McDaniel College
Westminster
8.4 out of 10, Very good, (8 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.
$410 nightly
The price is $434
Sep 24 - Sep 25
Total with taxes and fees
Green Street Oasis – Walk to Downtown Westminster & McDaniel College
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 24 - Sep 25
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
A bedroom with a sloped ceiling, floral wallpaper, a bed with a blue quilt, two bedside lamps, and framed floral artwork.

3. The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
$184 nightly
The price is $195
Oct 7 - Oct 8
Total with taxes and fees
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

4. 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 24 - Sep 25
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

5. 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.
$370 nightly
The price is $392
Sep 28 - Sep 29
Total with taxes and fees
Private Sauna, Fireplace and Country Views
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

6. 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.
$257 nightly
The price is $284
Sep 24 - Sep 25
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
A spacious room with large windows, a ceiling fan, and a modern chair.

7. 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, (52 reviews)
"Everything was great!"
United States
Corey G.
$569 nightly
The price is $628
Sep 24 - Sep 25
Total with taxes and fees
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

8. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (103 reviews)
"Great place!"
United States
Danielle G.
$314 nightly
The price is $333
Sep 28 - Sep 29
Total with taxes and fees
Modern Condo Right off Market Street
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

9. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 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.
$466 nightly
The price is $494
Sep 26 - Sep 27
Total with taxes and fees
Newly constructed 6 bedroom home
A ping pong table in a room with a television, a plant, and a sofa.

10. 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.
$140 nightly
The price is $148
Sep 24 - Sep 25
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A park with a pond, a bridge, and a church in the background.

11. 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, (141 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
$275 nightly
The price is $292
Sep 29 - Sep 30
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

12. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (13 reviews)
$134 nightly
The price is $148
Sep 27 - Sep 28
Total with taxes and fees
Cozy studio charming Hanover
A two-story white house with a balcony, a stone foundation, and an American flag.

13. Cozy Farmhouse with Fire Pit & Peaceful Country Views in Hanover, Pennsylvania

Cozy Farmhouse with Fire Pit & Peaceful Country Views in Hanover, Pennsylvania
Hanover
$782 nightly
The price is $864
Sep 24 - Sep 25
Total with taxes and fees
Cozy Farmhouse with Fire Pit & Peaceful Country Views in Hanover, Pennsylvania
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.

14. 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 27 - Sep 28
Total with taxes and fees
Newly Renovated Cozy Basement w/Private Entrance
A living room with a large mirror, a sofa, a television, and decorative items.

15. 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.
$281 nightly
The price is $298
Sep 27 - Sep 28
Total with taxes and fees
Downtown Frederick retreat with parking. Dog- and baby-friendly!
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (70 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
$252 nightly
The price is $267
Sep 28 - Sep 29
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

17. 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.
$210 nightly
The price is $223
Sep 29 - Sep 30
Total with taxes and fees
Cozy, dog-friendly, downtown
A brick building with a waterfall feature in front.

18. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 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.
$412 nightly
The price is $437
Oct 6 - Oct 7
Total with taxes and fees
New townhouse

19. DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall

DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
Gaithersburg
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay home was amazing "
United States
Darinda h.
$739 nightly
The price is $835
Sep 24 - Sep 25
Total with taxes and fees
DC Luxury Family Retreat in Forest—Spacious Full of Fun w/ Zipline Waterfall
A backyard with a hot tub, outdoor seating, and umbrellas.

20. Applewood Landing

Applewood Landing
Gettysburg
9.6 out of 10, Exceptional, (20 reviews)
"Enough room for our whole group."
United States
Anonymous traveler
$1,251 nightly
The price is $1,326
Oct 20 - Oct 21
Total with taxes and fees
Applewood Landing
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

Comfort Suites Near Gettysburg Battlefield Visitor Center

Comfort Suites Near Gettysburg Battlefield Visitor Center

10/10 Excellent
"We had a very enjoyable stay at the Comfort Inn in Gettysburg, Pennsylvania. The hotel was clean, comfortable, and in a great location for exploring Gettysburg and the surrounding historic sites. The room was spacious and comfortable, and the staff were friendly, welcoming, and helpful throughout our stay. We also appreciated the convenient location, which made it easy to get to the battlefield, visitor center, restaurants, and other attractions. The complimentary breakfast was a nice added convenience, and overall we felt the hotel offered good value for the price. We really enjoyed our stay and would be happy to return the next time we visit Gettysburg. I would definitely recommend this hotel to anyone looking for a comfortable and convenient place to stay."
Stephen 3-night trip
Posted 3 hours ago
Comfort Suites Near Gettysburg Battlefield Visitor 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 $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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: You might want to consider this vacation home rental near New Windsor, which 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.