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New Windsor Vacation Rentals

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Our top choices for New Windsor vacation rentals

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 CA $158
CA $397 total
includes taxes & fees
Jul 6 - Jul 7
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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 CA $178
CA $401 total
includes taxes & fees
Jul 12 - Jul 13
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

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 CA $114
CA $306 total
includes taxes & fees
Aug 4 - Aug 5
Pet-friendly, heart of downtown

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 CA $145
CA $348 total
includes taxes & fees
Jul 27 - Jul 28
Huge 1br apt, baby-friendly, dogs, walkable downtown

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 CA $172
CA $626 total
includes taxes & fees
Jul 6 - Jul 7
Rural & Historic Detour Escape w/ Horses On-Site!

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 CA $127
CA $210 total
includes taxes & fees
Jul 9 - Jul 10
Cozy studio charming Hanover

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 CA $114
CA $309 total
includes taxes & fees
Jul 6 - Jul 7
Cozy, dog-friendly, downtown

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is CA $231
CA $614 total
includes taxes & fees
Jul 6 - Jul 7
Rural & Historic Detour Escape w/ Horses On-site!

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, (14 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is CA $95
CA $304 total
includes taxes & fees
Jul 6 - Jul 7
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

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 CA $198
CA $460 total
includes taxes & fees
Jul 13 - Jul 14
Luxury Condo In Downtown Frederick

Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (98 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 CA $171
CA $401 total
includes taxes & fees
Jul 13 - Jul 14
Modern Condo Right off Market Street

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, (46 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is CA $133
CA $349 total
includes taxes & fees
Aug 4 - Aug 5
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

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 CA $234
CA $456 total
includes taxes & fees
Aug 4 - Aug 5
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

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 CA $216
CA $658 total
includes taxes & fees
Jul 6 - Jul 7
Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking

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 CA $142
CA $211 total
includes taxes & fees
Jul 13 - Jul 14
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV

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 CA $217
CA $330 total
includes taxes & fees
Jul 6 - Jul 7
Cozy Guesthouse in Woodstock, MD

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 CA $284
CA $545 total
includes taxes & fees
Jul 12 - Jul 13
Peaceful renovated Cabin in serene Westminster with AC, firepit on 5 Acres

Cozy & inviting 2BD 2BTH Apt Home

Cozy & inviting 2BD 2BTH Apt Home
Owings Mills
The price is CA $201
CA $404 total
includes taxes & fees
Jul 13 - Jul 14
Cozy & inviting 2BD 2BTH Apt Home

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
The price is CA $320
CA $785 total
includes taxes & fees
Jul 6 - Jul 7
Secret' Desires-Adult Only

New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (11 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is CA $242
CA $595 total
includes taxes & fees
Jul 6 - Jul 7
New townhouse
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

Find out more about New Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with New Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.