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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for New Windsor vacation rentals

A wooden deck with a fire pit, outdoor furniture, and string lights.

1. Paws, Pizza & Patio | Private Oasis Westminster

Paws, Pizza & Patio | Private Oasis Westminster
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 ￥61,586
￥74,664 total
includes taxes & fees
Oct 21 - Oct 22
Paws, Pizza & Patio | Private Oasis Westminster
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is ￥25,767
￥68,309 total
includes taxes & fees
Oct 20 - Oct 21
Rural & Historic Detour Escape w/ Horses On-site!
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!
Detour
9.0 out of 10, Wonderful, (8 reviews)
"Lovely! Our host was gracious and helpful. Property was ideal for our family getaway. i’m"
United States
Mary F.
The price is ￥19,128
￥69,540 total
includes taxes & fees
Oct 20 - Oct 21
Rural & Historic Detour Escape w/ Horses On-Site!
A cozy room with a dining table set, a sofa, a bed, and a window with curtains.

4. 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 ￥19,634
￥30,866 total
includes taxes & fees
Oct 16 - Oct 17
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A corner room with a sliding glass door closet, a wooden cabinet with glass doors, and a small rug on the floor.

5. Private Sauna, Fireplace and Country Views

Private Sauna, Fireplace and Country Views
Mount Airy
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful location with a beautiful field where wild animals visited. Hosts really took care of the amenities (great coffee bar). Close to Mt Airy and vineyards."
United States
Richard B.
The price is ￥52,562
￥62,921 total
includes taxes & fees
Oct 19 - Oct 20
Private Sauna, Fireplace and Country Views
A covered patio area with outdoor furniture, a grill, and a stone wall.

6. Hot Tub Farmhouse | Near Gettysburg | Sleeps 11

Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
Littlestown
10.0 out of 10, Exceptional, (20 reviews)
"Very comfortable stay for our family! "
United States
Becci
Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
A ping pong table in a room with a television, a plant, and a sofa.

7. 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 ￥15,808
￥23,459 total
includes taxes & fees
Oct 18 - Oct 19
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.

8. 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 ￥11,876
￥35,247 total
includes taxes & fees
Oct 20 - Oct 21
Cozy, dog-friendly, downtown
A living room with a black sofa, a glass table with chairs, a kitchen area with a refrigerator, and a ceiling fan.

9. Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA

Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Hanover
9.6 out of 10, Exceptional, (7 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 ￥19,760
￥44,843 total
includes taxes & fees
Oct 16 - Oct 17
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

10. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (105 reviews)
"The place was conveniently located within walking distance to downtown. Place was clean with parking space in back. Had a great stay."
United States
jeff h.
The price is ￥27,219
￥54,699 total
includes taxes & fees
Oct 19 - Oct 20
Modern Condo Right off Market Street
A storefront with a large glass window, a wooden door, and a brick sidewalk.

11. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (13 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

12. 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 ￥33,671
￥78,085 total
includes taxes & fees
Oct 18 - Oct 19
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is ￥22,922
￥46,751 total
includes taxes & fees
Nov 3 - Nov 4
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A modern kitchen with grey cabinets, a central island, and pendant lighting.

14. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is ￥25,467
￥55,482 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Condo In Downtown Frederick
A brick building with a waterfall feature in front.

15. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 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 ￥28,028
￥67,077 total
includes taxes & fees
Oct 21 - Oct 22
New townhouse
Living area

16. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
9.0 out of 10, Wonderful, (14 reviews)
"Place was as described. "
United States
Katie F.
The price is ￥14,085
￥23,374 total
includes taxes & fees
Oct 18 - Oct 19
Cozy studio charming Hanover
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.

17. 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 ￥16,915
￥23,189 total
includes taxes & fees
Nov 9 - Nov 10
Newly Renovated Cozy Basement w/Private Entrance
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

18. 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, (143 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is ￥22,131
￥49,431 total
includes taxes & fees
Nov 1 - Nov 2
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A storefront with a sign reading "PERENNIAL" and "CLAY & GARDEN".

19. The Wedgewood Inn / Historic Frederick Maryland

The Wedgewood Inn / Historic Frederick Maryland
Downtown Frederick
9.8 out of 10, Exceptional, (36 reviews)
"Exactly as pictured, great location, and great hosts!"
United States
Ann L.
The price is ￥35,568
￥66,691 total
includes taxes & fees
Oct 27 - Oct 28
The Wedgewood Inn / Historic Frederick Maryland
A living room with a large mirror, a sofa, a television, and decorative items.

20. 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, (8 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 ￥15,334
￥43,232 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Frederick retreat with parking. Dog- and baby-friendly!
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

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Good value for a quick night’s sleep while traveling through the area."
Frank 1-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Frederick, MD

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
  • Use the map to find apartments and other holiday homes in the New Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Windsor while they last

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?

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.