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New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for New Windsor vacation rentals

A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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

Rural & Historic Detour Escape w/ Horses On-Site!
Detour
9.0 out of 10, Wonderful, (8 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 1,604 total
includes taxes & fees
1 Oct - 2 Oct
Rural & Historic Detour Escape w/ Horses On-Site!
A wooden deck with a metal railing, a window with a view of trees, and a red bench.

2. The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
The price is AED 456
AED 717 total
includes taxes & fees
7 Oct - 8 Oct
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

3. 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 599
AED 1,587 total
includes taxes & fees
1 Oct - 2 Oct
Rural & Historic Detour Escape w/ Horses On-site!
A ping pong table in a room with a television, a plant, and a sofa.

4. 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
8.0 out of 10, Very good, (2 reviews)
"The stay was at a beautiful new home. Great host. Location close to Interstate 70. I had everything I needed. Took in the sights in DC via the Greenline Metro. I would definitely stay here again."
United States
Scott C.
The price is AED 367
AED 545 total
includes taxes & fees
5 Oct - 6 Oct
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

5. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
The price is AED 275
AED 818 total
includes taxes & fees
1 Oct - 2 Oct
Cozy, dog-friendly, downtown
A wooden deck with a fire pit, outdoor furniture, and string lights.

6. Green Street Oasis – Walk to Downtown Westminster & McDaniel College

Green Street Oasis – Walk to Downtown Westminster & McDaniel College
Westminster
8.4 out of 10, Very good, (8 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 AED 1,431
AED 1,723 total
includes taxes & fees
1 Oct - 2 Oct
Green Street Oasis – Walk to Downtown Westminster & McDaniel College
A modern apartment with a living room, kitchen, and dining area.

7. 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.
Pet-friendly, heart of downtown
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

8. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (2 reviews)
"Very comfortable and convenient stay with responsive hosts. Great amenities for longer stays with the w/d. Will be back!"
United States
Dave T.
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A kitchen with two stainless steel sinks, a window with a plant, and a white door.

9. 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, (17 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
The price is AED 240
AED 777 total
includes taxes & fees
4 Oct - 5 Oct
Patty's Place - Private and Convenient Apartment near Downtown
A modern hotel room with a large bed, two bedside tables, a flat-screen TV, a seating area with a chair and a small table, and a decorative plant.

10. Newly Renovated Cozy Basement w/Private Entrance

Newly Renovated Cozy Basement w/Private Entrance
Reisterstown
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay for the night."
United States
Sheila K.
The price is AED 459
AED 615 total
includes taxes & fees
1 Oct - 2 Oct
Newly Renovated Cozy Basement w/Private Entrance
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

11. 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 AED 459
AED 1,042 total
includes taxes & fees
1 Oct - 2 Oct
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
A patio area with a wooden table, chairs, a decorative vase, and a fire pit.

12. 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, (52 reviews)
"Great lodging and communicative host"
United States
Peggy D.
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

13. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is AED 782
AED 1,826 total
includes taxes & fees
4 Oct - 5 Oct
Newly constructed 6 bedroom home
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

14. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (70 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is AED 446
AED 975 total
includes taxes & fees
7 Oct - 8 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Living area

15. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (13 reviews)
"Place was as described. "
United States
Katie F.
The price is AED 327
AED 543 total
includes taxes & fees
1 Oct - 2 Oct
Cozy studio charming Hanover
A living room with a large mirror, a sofa, a television, and decorative items.

16. Downtown Frederick retreat with parking. Dog- and baby-friendly!

Downtown Frederick retreat with parking. Dog- and baby-friendly!
Frederick
9.8 out of 10, Exceptional, (7 reviews)
"This place looked exactly like the photos, very clean, super organized, and well designed. We were very comfortable during our stay and would stay here again."
United States
Dvorak A.
The price is AED 331
AED 973 total
includes taxes & fees
1 Oct - 2 Oct
Downtown Frederick retreat with parking. Dog- and baby-friendly!
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

17. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (141 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AED 775
AED 1,448 total
includes taxes & fees
23 Oct - 24 Oct
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

18. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (4 reviews)
"The property is excellent! Beautiful and peaceful surroundings. It was clean warm and welcoming. It’s pet friendly though we didn’t travel with pets. Outstanding host!"
United States
David M.
The price is AED 1,286
AED 1,550 total
includes taxes & fees
19 Oct - 20 Oct
Private Sauna, Fireplace and Country Views
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

19. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (103 reviews)
"Great place!"
United States
Danielle G.
The price is AED 668
AED 1,304 total
includes taxes & fees
5 Oct - 6 Oct
Modern Condo Right off Market Street
Fireplace Credenza

20. Shamrock Loft | Market St Frederick, MD

Shamrock Loft | Market St Frederick, MD
Downtown Frederick
The price is AED 375
AED 475 total
includes taxes & fees
26 Oct - 27 Oct
Shamrock Loft | Market St Frederick, MD
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

Turf Valley Resort

Turf Valley Resort

10/10 Excellent
"Excellent suite with a golfers dream view. The restaurant was great, excellent food and friendly staff."
Ron 3-night trip
Posted 4 hours ago
Turf Valley Resort

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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: You might want to consider this vacation home rental near New Windsor, which is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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.