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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for New Windsor vacation rentals

Smart TV

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 ￥10,722
￥32,718 total
includes taxes & fees
Aug 3 - Aug 4
Pet-friendly, heart of downtown
1 bedroom, WiFi (free), bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (33 reviews)
"Great location, clean place. "
United States
Warren B.
The price is ￥12,346
￥34,611 total
includes taxes & fees
Aug 4 - Aug 5
Cozy, dog-friendly, downtown
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, (10 reviews)
"Great little place for a weekend stay. Close to everything."
United States
Kurt S.
The price is ￥12,184
￥34,440 total
includes taxes & fees
Aug 3 - Aug 4
Huge 1br apt, baby-friendly, dogs, walkable downtown
Fridge, microwave, coffee/tea maker, toaster

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, (14 reviews)
"This was a wonderful stay and if the opportunity arises I’d love to come back "
United States
Amang
The price is ￥13,738
￥38,295 total
includes taxes & fees
Jul 21 - Jul 22
Patty's Place - Private and Convenient Apartment near Downtown
Smart TV

Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
8.6 out of 10, Excellent, (10 reviews)
"I stayed for a week while in town for work. Everything was very clean and the space was exactly what I needed. I believe I saw on another review about the gradual drop in the ceiling as you move from the kitchen into the living room so that is the only thing to watch out for. I’m 6’1 and managed it just fine. Would stay again! "
United States
Jonathan M.
The price is ￥14,456
￥23,989 total
includes taxes & fees
Aug 10 - Aug 11
Cozy studio charming Hanover
Game 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
6.0 out of 10, (1 review)
"The unit is in the basement of a beautiful single family home. The unit is accessed by going through the living room and going down the steps with no separate door for the unit. The kitchen is a shared space. The laundry is shared and accessed by by going through the basement space. There are 3 electric recliners and a projection screen TV. The sofa opens into a bed (no mattress). The unit would be best for someone who is comfortable with shared space."
United States
Paul H.
The price is ￥16,224
￥24,076 total
includes taxes & fees
Jul 21 - Jul 22
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
House (3 Bedrooms) | 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 ￥26,445
￥70,107 total
includes taxes & fees
Jul 26 - Jul 27
Rural & Historic Detour Escape w/ Horses On-site!
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, (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 ￥18,252
￥43,428 total
includes taxes & fees
Aug 14 - Aug 15
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
A park with a pond, a bridge, and a church in the background.

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, (130 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is ￥16,062
￥42,478 total
includes taxes & fees
Jul 16 - Jul 17
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
1 bedroom, iron/ironing board, WiFi, bed sheets

Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
10.0 out of 10, Exceptional, (1 review)
"Great place to stay for the night."
United States
Sheila K.
The price is ￥17,522
￥23,986 total
includes taxes & fees
Aug 2 - Aug 3
Newly Renovated Cozy Basement w/Private Entrance
Interior

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.6 out of 10, Exceptional, (4 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 ￥19,631
￥71,197 total
includes taxes & fees
Jul 20 - Jul 21
Rural & Historic Detour Escape w/ Horses On-Site!
Smart TV, fireplace, books, music library

Peaceful renovated Cabin in serene Westminster with AC, firepit on 5 Acres

Peaceful renovated Cabin in serene Westminster with AC, firepit on 5 Acres
Westminster
The price is ￥27,617
￥55,620 total
includes taxes & fees
Jul 16 - Jul 17
Peaceful renovated Cabin in serene Westminster with AC, firepit on 5 Acres
Apartment (4 Bedrooms) | Interior

Frederick Townhome w/ Balcony, Close to Parks!

Frederick Townhome w/ Balcony, Close to Parks!
4.0 star property
Frederick
The price is ￥48,248
￥91,167 total
includes taxes & fees
Jul 31 - Aug 1
Frederick Townhome w/ Balcony, Close to Parks!
Property grounds

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, (5 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 ￥36,828
￥73,661 total
includes taxes & fees
Jul 21 - Jul 22
Backyard Oasis | Swim Spa, Fire Pit & Relaxing Outdoor Retreat
Coffee/tea maker, fridge, microwave, oven

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Communication with the host was great. The host was very responsive and helpful with an early check in. The property was updated and very comfortable. Perfect place to stay for a young family or small group. Perfect location to beautiful downtown Frederick."
United States
Matthew C.
The price is ￥21,200
￥48,129 total
includes taxes & fees
Jul 20 - Jul 21
Modern Condo Right off Market Street
Coffee/tea maker, fridge, microwave, oven

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (68 reviews)
"Everything was very clean and comfortable. The kitchen was well equipped."
United States
Linda D.
The price is ￥20,469
￥44,599 total
includes taxes & fees
Jul 21 - Jul 22
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Outdoor dining

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
9.8 out of 10, Exceptional, (48 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is ￥21,119
￥47,010 total
includes taxes & fees
Jul 20 - Jul 21
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Interior

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fairfield
9.8 out of 10, Exceptional, (51 reviews)
"Everything was great!"
United States
Corey G.
The price is ￥64,896
￥101,893 total
includes taxes & fees
Aug 14 - Aug 15
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Fridge, microwave, oven, stovetop

Peaceful Hollow - Peaceful Hollow

Peaceful Hollow - Peaceful Hollow
Manchester
10.0 out of 10, Exceptional, (41 reviews)
"Beautiful location, property well kept, very clean and cozy would definitely come again"
United States
Haim H.
The price is ￥58,396
￥107,704 total
includes taxes & fees
Jul 16 - Jul 17
Peaceful Hollow - Peaceful Hollow
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (96 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is ￥22,486
￥52,900 total
includes taxes & fees
Jul 21 - Jul 22
Luxury Condo In Downtown Frederick
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
"Stayed for short stay for a wedding and it was great!!!"
Ahuvah 1-night trip
Posted 5 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:

  • 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 vacation rentals in New Windsor?

Yes, we give you a choice of vacation rentals near well known points of interest in New Windsor, or you can go with a more secluded option if you want a relaxing place to 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 vacation home rentals in New Windsor?

“The Train Depot” 2nd oldest in the US: Visitors like this New Windsor vacation home rental. It is located in the city center 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 vacation 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 larger area, you’ll find Old Westminster Winery and Elk Run Vineyards.

What’s a vacation rental in New Windsor like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in New Windsor. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.