New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for New Windsor holiday rentals

Games room

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
The price is HK$783
HK$1,162 total
includes taxes & fees
11 May - 12 May
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Great location, clean place. "
United States
Warren B.
The price is HK$536
HK$1,564 total
includes taxes & fees
11 May - 12 May
Cozy, dog-friendly, downtown
TV

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

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.0 out of 10, Wonderful, (4 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$979
HK$2,221 total
includes taxes & fees
13 May - 14 May
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

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, (126 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is HK$775
HK$2,017 total
includes taxes & fees
10 Jun - 11 Jun
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Smart TV

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.2 out of 10, Wonderful, (5 reviews)
"This place was great. Ceiling is low, less that 6 feet in some spots. Location is great for visiting downtown Hanover. Parking was convenient. Stayed overnight with a buddy. Brought an air mattress so we didn’t have to share a bed (couch would’ve been a little small for sleeping comfortably)."
United States
Tim
The price is HK$698
HK$1,158 total
includes taxes & fees
14 May - 15 May
Cozy studio charming Hanover
Smart TV

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 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$619
HK$1,676 total
includes taxes & fees
9 Jun - 10 Jun
Pet-friendly, heart of downtown
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (27 reviews)
"We had a very nice stay here, kitchen and bathroom had all necessary amenities provided. Cozy cabin, a little chilly at night but blankets were provided as well so it was OK."
United States
Emily Z.
The price is HK$775
HK$1,195 total
includes taxes & fees
24 May - 25 May
Birch Cabin at Hunting Creek Hideaway
Exterior detail

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

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Great little place for a weekend stay. Close to everything."
United States
Kurt S.
The price is HK$893
HK$2,025 total
includes taxes & fees
2 Jun - 3 Jun
Huge 1br apt, baby-friendly, dogs, walkable downtown
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (68 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is HK$1,135
HK$2,324 total
includes taxes & fees
26 May - 27 May
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
1 bedroom, iron/ironing board, WiFi, bed sheets

Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
The price is HK$740
HK$1,035 total
includes taxes & fees
27 May - 28 May
Newly Renovated Cozy Basement w/Private Entrance
TV, table football, books

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
The price is HK$627
HK$1,329 total
includes taxes & fees
12 May - 13 May
Cozy Pine Tree Nest
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (87 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is HK$1,261
HK$2,582 total
includes taxes & fees
11 May - 12 May
Luxury Condo In Downtown Frederick
Fridge, microwave, oven, stovetop

Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays

Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays
Westminster
8.4 out of 10, Very good, (6 reviews)
"We enjoyed our stay, spacious rooms and cute decor. "
United States
Anonymous traveller
The price is HK$1,173
HK$2,439 total
includes taxes & fees
11 May - 12 May
Spacious 5 BR Stay in Westminster | Perfect for Groups & Longer Stays
Outdoor dining

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, (41 reviews)
"Immaculate apartment conveniently located close to Frederick Health Hospital in a quiet residential neighborhood. Just a fifteen minute walk to the heart of Frederick for memorable dining, interesting shops, and cozy cafés."
United States
Mark L.
The price is HK$979
HK$2,200 total
includes taxes & fees
11 May - 12 May
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Exterior

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (10 reviews)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
The price is HK$1,184
HK$2,823 total
includes taxes & fees
12 May - 13 May
New townhouse
Property grounds

Private Pool Getaway

Private Pool Getaway
Owings Mills
The price is HK$775
HK$1,709 total
includes taxes & fees
11 May - 12 May
Private Pool Getaway
Interior

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$1,057
HK$3,379 total
includes taxes & fees
11 May - 12 May
Rural & Historic Detour Escape w/ Horses On-site!
Microwave, oven, stovetop, dishwasher

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
The price is HK$1,018
HK$2,884 total
includes taxes & fees
11 May - 12 May
Secret' Desires-Adult Only
Fridge, microwave, oven, stovetop

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (90 reviews)
"Very clean and good location. "
United States
Kerry H.
The price is HK$1,261
HK$2,582 total
includes taxes & fees
11 May - 12 May
Modern Condo Right off Market Street
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.4 out of 10, Exceptional, (3 reviews)
"Check-in was super easy. Communication with the owners was quick and easy. There was one hiccup that came up and were very quick to resolve. The house itself is a great historic home. They have done a great job modernizing it. My only feedback would be to have more supplies in the kitchen to accommodate preparing foods like knives, cutting boards, trays, etc. But otherwise, very happy with our stay and the beautiful property, and it being dog friendly!"
United States
Rachel W.
The price is HK$940
HK$3,424 total
includes taxes & fees
11 May - 12 May
Rural & Historic Detour Escape w/ Horses On-Site!
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

Budget Host Three Crowns Motor Lodge

Budget Host Three Crowns Motor Lodge

8/10 Good
"Charming little hotel right in the middle of town. Excellent service and recommendations.easy access to many attractions."
Peter 1-night trip
Posted 2 hours ago
Budget Host Three Crowns Motor Lodge

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:

  • View our selection of featured holiday rentals in New Windsor
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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?

Historic Bucher House with central location to Gettysburg and Lancaster Amish: This holiday home rental outside of New Windsor is located in the city centre, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.