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New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for New Windsor holiday rentals

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

1. Paws, Pizza & Patio | Private Oasis Westminster

Paws, Pizza & Patio | Private Oasis Westminster
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.
The price is AU$650
includes taxes & fees
22 Oct - 23 Oct
Paws, Pizza & Patio | Private Oasis Westminster
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!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is AU$616
includes taxes & fees
3 Nov - 4 Nov
Rural & Historic Detour Escape w/ Horses On-Site!
A cozy room with a dining table set, a sofa, a bed, and a window with curtains.

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

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
The price is AU$281
includes taxes & fees
25 Oct - 26 Oct
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!
3.0 star property
Keymar
The price is AU$616
includes taxes & fees
25 Oct - 26 Oct
Rural & Historic Detour Escape w/ Horses On-site!
A ping pong table in a room with a television, a plant, and a sofa.

5. 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.
The price is AU$215
includes taxes & fees
25 Oct - 26 Oct
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.

6. 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.
The price is AU$319
includes taxes & fees
22 Oct - 23 Oct
Cozy, dog-friendly, downtown
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

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

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.6 out of 10, Exceptional, (7 reviews)
"Great location in downtown Hanover within walking distance of the square where there are various shops and dining options. "
United States
Danna W.
The price is AU$401
includes taxes & fees
22 Oct - 23 Oct
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Living area

8. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (14 reviews)
"Place was as described. "
United States
Katie F.
The price is AU$214
includes taxes & fees
22 Oct - 23 Oct
Cozy studio charming Hanover
A living room with a fireplace, two sofas, a patterned rug, and framed artwork on the walls.

9. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (6 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.
The price is AU$554
includes taxes & fees
26 Oct - 27 Oct
Private Sauna, Fireplace and Country Views
A modern apartment with a living room, kitchen, and dining area.

10. Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is AU$336
includes taxes & fees
22 Oct - 23 Oct
Pet-friendly, heart of downtown
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

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

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (5 reviews)
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A covered patio area with outdoor furniture, a grill, and a stone wall.

12. Hot Tub Farmhouse | Near Gettysburg | Sleeps 11

Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
Littlestown
10.0 out of 10, Exceptional, (20 reviews)
"We loved the quiet location, and while the house felt wonderfully quaint, it was beautifully updated inside. The space was incredibly clean and the kitchen had everything we needed. Highly recommended if you want to relax!"
United States
Carolyn W.
Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
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.

13. 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.
The price is AU$212
includes taxes & fees
8 Nov - 9 Nov
Newly Renovated Cozy Basement w/Private Entrance
A living room with a large mirror, a sofa, a television, and decorative items.

14. 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, (8 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.
The price is AU$403
includes taxes & fees
25 Oct - 26 Oct
Downtown Frederick retreat with parking. Dog- and baby-friendly!
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

15. 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.
The price is AU$706
includes taxes & fees
28 Oct - 29 Oct
Newly constructed 6 bedroom home
A cozy living room with a ceiling fan, a black leather sofa, a coffee table, and a wooden ladder.

16. 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.
The price is AU$338
includes taxes & fees
28 Oct - 29 Oct
Cozy Guesthouse in Woodstock, MD
Property grounds

17. Entire lower level furnished home

Entire lower level furnished home
Owings Mills
2.0 out of 10, (2 reviews)
"Our reservation was cancelled because the owner never provided check in instructions, never responded to messages or phone calls. Drove almost to the house when VRBO office staff was able to help us. We were stranded! Definitely not a reputable owner!!! Stay clear of this property!"
United States
Megan K. K.
The price is AU$404
includes taxes & fees
22 Oct - 23 Oct
Entire lower level furnished home
A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

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.
The price is AU$604
includes taxes & fees
27 Oct - 28 Oct
New townhouse
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

19. 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, (145 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AU$439
includes taxes & fees
8 Nov - 9 Nov
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is AU$424
includes taxes & fees
27 Oct - 28 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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

Home2 Suites by Hilton Owings Mills

Home2 Suites by Hilton Owings Mills

10/10 Excellent
"Nice clean rooms. The hotel was well maintained. The furniture my room was a little dated but very clean. I would stay there again."
ROBERT 1-night trip
Posted 14 hours ago
Home2 Suites by Hilton Owings Mills

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, 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 favourite 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 depend 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 AU$439 per night. Entering your travel dates in the search wizard might find you 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.