Holiday Rentals New Windsor from £115: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for New Windsor holiday 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!

Detour

Charla H.

includes taxes & fees

1 Oct - 2 Oct

A wooden deck with a metal railing, a window with a view of trees, and a red bench.

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

Westminster

includes taxes & fees

13 Oct - 14 Oct

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

Keymar

includes taxes & fees

1 Oct - 2 Oct

A ping pong table in a room with a television, a plant, and a sofa.

4. Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

Woodbine

Scott C.

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

5. Cozy, dog-friendly, downtown

Frederick

Warren B.

includes taxes & fees

1 Oct - 2 Oct

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

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

Westminster

Payson D.

includes taxes & fees

1 Oct - 2 Oct

A modern apartment with a living room, kitchen, and dining area.

7. Pet-friendly, heart of downtown

Frederick

nikki b.

A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

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

Downtown Frederick

Dave T.

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Top New Windsor Hotel Reviews

Hyatt Place Baltimore/Owings Mills

8/10 Good

"Rooms are recently updated. Breakfast was just ok, have had better free hotel breakfasts."

Holiday Inn Express and Suites Gettysburg by IHG

8/10 Good

"Staff was friendly and helpful. Location was close to Gettysburg and the battlefield. It was a little tricky finding the building but once we did it was easy after that. Breakfast had a lot of choices and was very tasty. The only disappointment was the pool- it appeared to need some attention, either cleaning or painting of the bottom. We will definitely consider going back again."

The Lodges at Gettysburg

10/10 Excellent

"This is a beautiful property with individual private lodges on a hilltop overlooking the countryside. The lodges are comfortably appointed with toiletries and a kitchen that has a refrigerator, microwave, coffee maker, dishes, and silverware. There is also a restaurant on the property, although it does not serve breakfast. The Eisenhower farm is less than three miles away."

Marriott Owings Mills Metro Centre

10/10 Excellent

"I really enjoyed my stay. The staff were amazing and the room was clean. This is the perfect spot to stay when visiting for the first time. The location was great because it is in the center and you can walk, catch the train and it's not far from shopping centers and restaurants. There is a shuttle that takes you 3 miles out and the drive is so nice and accommodating."

Find out more about New Windsor

Everything you need to know about New Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Windsor holiday rentals we have selected for you start as low as £115 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor holiday 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 holiday.

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 holiday rentals in New Windsor?

Yes, there are holiday rentals close to the most popular sights in New Windsor, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that New Windsor has to offer?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This holiday home rental outside of New Windsor is located in the city centre, 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find Old Westminster Winery and Carroll County Farm Museum.

What’s a holiday rental in New Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in New Windsor. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for small groups.

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Check prices for these dates

Our top choices for New Windsor holiday rentals

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

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

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