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New Windsor Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for New Windsor holiday rentals

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 HK$871
HK$2,137 total
includes taxes & fees
6 Jul - 7 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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 HK$980
HK$2,225 total
includes taxes & fees
12 Jul - 13 Jul
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
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 HK$604
HK$1,663 total
includes taxes & fees
6 Jul - 7 Jul
Pet-friendly, heart of 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 HK$800
HK$1,846 total
includes taxes & fees
27 Jul - 28 Jul
Huge 1br apt, baby-friendly, dogs, walkable downtown
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 HK$949
HK$3,422 total
includes taxes & fees
6 Jul - 7 Jul
Rural & Historic Detour Escape w/ Horses On-Site!
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 HK$699
HK$1,160 total
includes taxes & fees
12 Jul - 13 Jul
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 HK$627
HK$1,688 total
includes taxes & fees
6 Jul - 7 Jul
Cozy, dog-friendly, downtown
Front of property

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$1,278
HK$3,389 total
includes taxes & fees
6 Jul - 7 Jul
Rural & Historic Detour Escape w/ Horses On-site!
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, (14 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is HK$527
HK$1,665 total
includes taxes & fees
6 Jul - 7 Jul
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (94 reviews)
"All amenities were top notch "
United States
John M.
The price is HK$1,108
HK$2,555 total
includes taxes & fees
15 Jul - 16 Jul
Luxury Condo In Downtown Frederick
Fridge, microwave, oven, stovetop

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 HK$946
HK$2,233 total
includes taxes & fees
13 Jul - 14 Jul
Modern Condo Right off Market Street
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, (46 reviews)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is HK$737
HK$1,871 total
includes taxes & fees
4 Aug - 5 Aug
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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)
"Everything was very clean and comfortable. The kitchen was well equipped."
United States
Linda D.
The price is HK$1,294
HK$2,486 total
includes taxes & fees
21 Jul - 22 Jul
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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 HK$1,192
HK$3,596 total
includes taxes & fees
6 Jul - 7 Jul
Elegant 3BR Apt / 4 Beds / 2 Bath / Wi-Fi / Free Parking
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
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 HK$784
HK$1,164 total
includes taxes & fees
13 Jul - 14 Jul
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
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 HK$1,200
HK$1,821 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Guesthouse in Woodstock, MD
2 bedrooms, desk, iron/ironing board, travel cot

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 HK$1,567
HK$3,024 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful renovated Cabin in serene Westminster with AC, firepit on 5 Acres
Private kitchen

Cozy & inviting 2BD 2BTH Apt Home

Cozy & inviting 2BD 2BTH Apt Home
Owings Mills
The price is HK$1,108
HK$2,213 total
includes taxes & fees
13 Jul - 14 Jul
Cozy & inviting 2BD 2BTH Apt Home
Microwave, oven, stovetop, dishwasher

Secret' Desires-Adult Only

Secret' Desires-Adult Only
Gaithersburg
The price is HK$1,961
HK$4,546 total
includes taxes & fees
6 Jul - 7 Jul
Secret' Desires-Adult Only
Exterior

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 HK$1,334
HK$3,235 total
includes taxes & fees
6 Jul - 7 Jul
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

Eisenhower Hotel & Conference Center

Eisenhower Hotel & Conference Center

10/10 Excellent
"good"
Edward 1-night trip
Posted 2 hours ago
Eisenhower Hotel & Conference Center

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?

“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 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.