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New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for New Windsor holiday rentals

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

1. Green Street Oasis – Walk to Downtown Westminster - Pet Friendly

Green Street Oasis – Walk to Downtown Westminster - Pet Friendly
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 HK$3,057
HK$3,681 total
includes taxes & fees
7 Oct - 8 Oct
Green Street Oasis – Walk to Downtown Westminster - Pet Friendly
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$1,279
HK$3,391 total
includes taxes & fees
19 Oct - 20 Oct
Rural & Historic Detour Escape w/ Horses On-site!
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

3. 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 HK$949
HK$3,427 total
includes taxes & fees
19 Oct - 20 Oct
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.

4. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (5 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 HK$2,707
HK$3,236 total
includes taxes & fees
2 Nov - 3 Nov
Private Sauna, Fireplace and Country Views
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

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

6. 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$785
HK$1,164 total
includes taxes & fees
12 Oct - 13 Oct
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A compact kitchen with a wooden table, white chairs, a coffee station, and a clock on the wall.

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
Patty's Place - Private and Convenient Apartment near Downtown
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.

8. 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 HK$981
HK$1,314 total
includes taxes & fees
7 Oct - 8 Oct
Newly Renovated Cozy Basement w/Private Entrance
A modern apartment with a living room, kitchen, and dining area.

9. 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$589
HK$1,739 total
includes taxes & fees
7 Oct - 8 Oct
Pet-friendly, heart of downtown
Living area

10. 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$1,160 total
includes taxes & fees
17 Oct - 18 Oct
Cozy studio charming Hanover
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

11. 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 HK$1,671
HK$3,884 total
includes taxes & fees
12 Oct - 13 Oct
Newly constructed 6 bedroom home
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

12. 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$981
HK$2,226 total
includes taxes & fees
7 Oct - 8 Oct
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
A storefront with a large glass window, a wooden door, and a brick sidewalk.

13. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (12 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
A GE front-loading washer and dryer unit with a stone wall background.

14. Chapel & Clover | Cozy Downtown Frederick Loft

Chapel & Clover | Cozy Downtown Frederick Loft
Downtown Frederick
The price is HK$651
HK$2,415 total
includes taxes & fees
3 Nov - 4 Nov
Chapel & Clover | Cozy Downtown Frederick Loft
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

15. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (104 reviews)
"Great place!"
United States
Danielle G.
The price is HK$1,285
HK$2,618 total
includes taxes & fees
7 Oct - 8 Oct
Modern Condo Right off Market Street
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
10.0 out of 10, Exceptional, (3 reviews)
"Very comfortable and convenient stay with responsive hosts. Great amenities for longer stays with the w/d. Will be back!"
United States
Dave T.
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

17. 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, (54 reviews)
"Great lodging and communicative host"
United States
Peggy D.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A modern kitchen with grey cabinets, a central island, and pendant lighting.

18. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is HK$1,222
HK$2,684 total
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo In Downtown Frederick
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.

19. 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.
The price is HK$953
HK$2,092 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A living room with a television on a wooden cabinet, a fireplace, and a sofa.

20. Shamrock Loft | Market St Frederick, MD

Shamrock Loft | Market St Frederick, MD
Downtown Frederick
The price is HK$643
HK$848 total
includes taxes & fees
26 Oct - 27 Oct
Shamrock Loft | Market St Frederick, MD
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

Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

10/10 Excellent
"Had issues with the toilet but it was taken care of immediately, it could not be repaired properly in a timely manner so we had to relocate to another room. Moving to another room was a bit of an inconvenience considering we had an event to go to with 30 minutes to get ready after the move."
Tabitha 1-night trip
Posted 12 hours ago
Hyatt Place Baltimore/Owings Mills

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.