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New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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!

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (7 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.
The price is HK$949
HK$3,432 total
includes taxes & fees
7 Sept - 8 Sept
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
The price is HK$1,278
HK$3,388 total
includes taxes & fees
7 Sept - 8 Sept
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.
The price is HK$784
HK$1,163 total
includes taxes & fees
5 Sept - 6 Sept
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.
Cozy, dog-friendly, downtown
A kitchen with two stainless steel sinks, a window with a plant, and a white door.

5. 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
The price is HK$630
HK$1,798 total
includes taxes & fees
10 Sept - 11 Sept
Patty's Place - Private and Convenient Apartment near Downtown
A modern apartment with a living room, kitchen, and dining area.

6. 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.
The price is HK$588
HK$1,645 total
includes taxes & fees
30 Sept - 1 Oct
Pet-friendly, heart of downtown
A covered outdoor patio with a table and chairs, a wooden deck, and a view of greenery.

7. Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (23 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
The price is HK$755
HK$2,088 total
includes taxes & fees
7 Sept - 8 Sept
Chic, pets, walk to downtown

8. 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.
The price is HK$699
HK$1,159 total
includes taxes & fees
6 Sept - 7 Sept
Cozy studio charming Hanover
A wooden deck with a fire pit, outdoor furniture, and string lights.

9. 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.
The price is HK$3,337
HK$4,019 total
includes taxes & fees
14 Sept - 15 Sept
Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

10. 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.
The price is HK$980
HK$2,224 total
includes taxes & fees
6 Sept - 7 Sept
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
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)
"Very clean and quiet studio. I would highly recommend."
United States
Jim S.
The price is HK$1,019
HK$1,358 total
includes taxes & fees
7 Sept - 8 Sept
Newly Renovated Cozy Basement w/Private Entrance
A living room with a large mirror, a sofa with cushions, a television, and decorative items on a wooden console.

12. 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.
The price is HK$800
HK$2,186 total
includes taxes & fees
10 Sept - 11 Sept
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.

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.
The price is HK$988
HK$2,119 total
includes taxes & fees
14 Sept - 15 Sept
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.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A park with a pond, a bridge, and a church in the background.

15. 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, (136 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is HK$870
HK$2,177 total
includes taxes & fees
13 Sept - 14 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

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

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
The price is HK$643
HK$1,886 total
includes taxes & fees
22 Sept - 23 Sept
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.

17. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (3 reviews)
"The house was very spacious. We cooked and ate dinner as a family of 8 and fit us nicely. The beds were comfy. Views from the dinning room windows were beautiful. Everything was clean. We enjoyed our stay."
United States
Wyatt Y.
The price is HK$2,611
HK$3,125 total
includes taxes & fees
8 Sept - 9 Sept
Private Sauna, Fireplace and Country Views
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

18. 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.
The price is HK$1,263
HK$2,602 total
includes taxes & fees
7 Sept - 8 Sept
Modern Condo Right off Market Street
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.
The price is HK$1,277
HK$2,758 total
includes taxes & fees
23 Sept - 24 Sept
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, (20 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 HK$1,670
HK$3,897 total
includes taxes & fees
5 Oct - 6 Oct
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.
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Top New Windsor Hotel Reviews

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Very nice spacious room and drinks facilities available from the dining area. Breakfast was very nice that included some hot food plus the normal continental options"
Paul 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about New Windsor

Search for holiday rentals in New Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in New Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in New Windsor!

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.