Default HTG hotel image

New Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for New Windsor vacation rentals

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)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is AED 680
AED 1,258 total
includes taxes & fees
21 Jul - 22 Jul
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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)
"Host was very flexible, communication was excellent. Perfect place to explore the area. "
United States
Dustin
The price is AED 459
AED 1,034 total
includes taxes & fees
25 Jun - 26 Jun
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
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 AED 496
AED 1,585 total
includes taxes & fees
25 Jun - 26 Jun
Rural & Historic Detour Escape w/ Horses On-site!
Microwave, oven, stovetop, dishwasher

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
The price is AED 918
AED 2,129 total
includes taxes & fees
25 Jun - 26 Jun
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, (96 reviews)
"Lovely, cozy apartment, more spacious than we imagined and the perfect place to retreat to after the bustling shops and restaurants a few blocks away."
United States
Alexandra W.
The price is AED 496
AED 1,094 total
includes taxes & fees
25 Jun - 26 Jun
Modern Condo Right off Market Street
2 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres

Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres
Westminster
The price is AED 744
AED 1,427 total
includes taxes & fees
1 Jul - 2 Jul
Cozy 2-bedroom renovated cabin in serene Westminster with AC on 5 Acres
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 AED 305
AED 790 total
includes taxes & fees
7 Jul - 8 Jul
Pet-friendly, heart of downtown
Property grounds

Cozy Guesthouse in Woodstock, MD

Cozy Guesthouse in Woodstock, MD
Woodstock
2.0 out of 10, (1 review)
"We didn’t stay. We when arrived, instead of a room in the guest house, we were expected to stay in a tentlike structure. In addition, the bathroom facilities were outdoor showers and commodes that required a climb up a set of stairs. Luckily we were able to secure a room at another facility. The owner supposedly requested a refund for me but I haven’t heard whether this has been approved."
United States
Marie E M.
The price is AED 562
AED 844 total
includes taxes & fees
25 Jun - 26 Jun
Cozy Guesthouse in Woodstock, MD
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 AED 1,469
AED 2,307 total
includes taxes & fees
30 Jun - 1 Jul
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (94 reviews)
"All amenities were top notch "
United States
John M.
The price is AED 592
AED 1,277 total
includes taxes & fees
30 Jun - 1 Jul
Luxury Condo In Downtown Frederick
Fridge, microwave, oven, stovetop

Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (18 reviews)
"Everything was excellent "
United States
Ronald G.
The price is AED 801
AED 1,744 total
includes taxes & fees
22 Jul - 23 Jul
Newly constructed 6 bedroom home

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, (129 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is AED 448
AED 1,040 total
includes taxes & fees
14 Jul - 15 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
TV, foosball, 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 AED 294
AED 623 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Pine Tree Nest
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (18 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 AED 395
AED 1,030 total
includes taxes & fees
1 Jul - 2 Jul
Chic, pets, walk to downtown
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, (44 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is AED 364
AED 919 total
includes taxes & fees
6 Jul - 7 Jul
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 stay was flawless and did not disappoint. The home was better than advertised and check in was painless. Would stay there again without hesitation!"
United States
Jeremy G.
The price is AED 944
AED 1,908 total
includes taxes & fees
25 Jun - 26 Jun
New townhouse
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 AED 327
AED 543 total
includes taxes & fees
25 Jun - 26 Jun
Cozy studio charming Hanover
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (32 reviews)
"Great location, clean place. "
United States
Warren B.
The price is AED 320
AED 829 total
includes taxes & fees
20 Jul - 21 Jul
Cozy, dog-friendly, downtown
Exterior

Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking

Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking
Garrison
9.0 out of 10, Wonderful, (2 reviews)
"The host was very responsive to questions prior to our arrival, as well as a few things during our stay. Was a great place for my family to stay with our two dogs, as well as plenty of room for local family to come for dinner and catch up. Great location with plenty of shops and food choices near by, as well as groceries stores to get stuff for the house. Would definitely stay here again if needed to."
United States
Carly L.
The price is AED 727
AED 2,142 total
includes taxes & fees
25 Jun - 26 Jun
Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking
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 AED 444
AED 1,618 total
includes taxes & fees
25 Jun - 26 Jun
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Windsor Hotel Reviews

Hilton Garden Inn Owings Mills

Hilton Garden Inn Owings Mills

10/10 Excellent
"Room was very clean and comfortable. Issues with the TV were quickly resolved."
Jenene 2-night trip
Posted 1 hour ago
Hilton Garden Inn Owings Mills

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 Winchester Park. In the larger area, you’ll find Old Westminster Winery and Carroll County Farm Museum.

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.