New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for New Windsor holiday rentals

TV

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

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.4 out of 10, Exceptional, (3 reviews)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
The price is HK$979
HK$2,214 total
includes taxes & fees
23 Mar - 24 Mar
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Smart TV

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
10.0 out of 10, Exceptional, (3 reviews)
"We were visiting York and needed a place to stay. This is about 1/2 hour out...and it was WONDERFUL. (1) The place was clean, (2) The space was perfect for my wife, myself and the dogs. The room was quiet. The shower was hot. Communication with the property owner/manager was wonderful. What a WONDERFUL stay. A I would not hesitate to go back.Things you should be aware of.. (1) They wrote that the ceiling is incredibly low...lol, and it actually is. I banged my head at one point. I am...
United States
James M.
The price is HK$698
HK$1,158 total
includes taxes & fees
22 Mar - 23 Mar
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$437
HK$1,460 total
includes taxes & fees
23 Mar - 24 Mar
Pet-friendly, heart of downtown
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
22 Mar - 23 Mar
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
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, (65 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is HK$917
HK$2,026 total
includes taxes & fees
24 Mar - 25 Mar
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Fridge, microwave, coffee/tea maker, toaster

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (6 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is HK$527
HK$1,638 total
includes taxes & fees
22 Mar - 23 Mar
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Dining

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (80 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is HK$606
HK$1,764 total
includes taxes & fees
23 Mar - 24 Mar
*Luxury Condo In Downtown Frederick*
Dining

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, (124 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$869
HK$2,126 total
includes taxes & fees
30 Mar - 31 Mar
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is HK$465
HK$1,490 total
includes taxes & fees
23 Mar - 24 Mar
Cozy, dog-friendly, downtown
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (84 reviews)
"The location was perfect - walking distance to everything we wanted to do in Frederick. The place was clean and comfortable for 2 couples. "
United States
N. N.
The price is HK$550
HK$1,704 total
includes taxes & fees
22 Mar - 23 Mar
*Modern Condo In Downtown Frederick*
Fridge, microwave, oven, stovetop

Gated 3BR Apartment in Westminster Private Parking

Gated 3BR Apartment in Westminster Private Parking
Westminster
8.0 out of 10, Very good, (5 reviews)
"We enjoyed our stay, spacious rooms and cute decor. "
United States
Anonymous traveller
The price is HK$1,090
HK$2,259 total
includes taxes & fees
26 Mar - 27 Mar
Gated 3BR Apartment in Westminster Private Parking
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, (39 reviews)
"Everything was very clean and tidy, and very bright. The beds were extremely comfortable. Location was perfect and we really enjoyed having the backyard with a hot tub and a fire pit very relaxing."
United States
Donna C.
The price is HK$839
HK$2,035 total
includes taxes & fees
22 Mar - 23 Mar
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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$3,381 total
includes taxes & fees
22 Mar - 23 Mar
Rural & Historic Detour Escape w/ Horses On-site!
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, (7 reviews)
"Host was very responsive before and during my stay. Apartment is beautifully appointed and has all the amenities you need for a great weekend stay!!"
United States
lizbeth g.
The price is HK$682
HK$1,719 total
includes taxes & fees
1 Apr - 2 Apr
Huge 1br apt, baby-friendly, dogs, walkable downtown
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay. The place has perfect and the location was close to everything downtown. The host was great. Will definitely stay there again."
United States
Patrick H.
Chic, pets, walk to downtown
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
4 Apr - 5 Apr
Cozy Pine Tree Nest
Exterior

New townhouse

New townhouse
Frederick
9.4 out of 10, Exceptional, (9 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$2,816 total
includes taxes & fees
24 Mar - 25 Mar
New townhouse
Fridge, microwave, oven, stovetop

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (14 reviews)
"Quiet and convenient stay in very comfortable house. Host was on top of every question and very helpful, answered questions immediately. Many thanks for a lovely stay."
United States
Janine S.
The price is HK$1,668
HK$3,628 total
includes taxes & fees
24 Mar - 25 Mar
Newly constructed 6 bedroom home
Microwave, oven, stovetop, dishwasher

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
The price is HK$1,018
HK$2,886 total
includes taxes & fees
24 Mar - 25 Mar
Secret' Desires-Adult Only
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
The price is HK$940
HK$3,343 total
includes taxes & fees
22 Mar - 23 Mar
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

Inn at Cemetery Hill

Inn at Cemetery Hill

10/10 Excellent
"The staff was EXCELLENT, so incredibly friendly. We did a ton of walking, and so many things are nearby. "
Megan 3-night trip
Posted 1 hour ago
Inn at Cemetery Hill

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?

“The Train Depot” 2nd oldest in the US: This holiday home rental outside of New Windsor is located in the city centre, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and 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 Elk Run Vineyards.

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.