New Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for New Windsor vacation rentals

A brick entrance with a dark wooden door, a small step leading up to it, and two signs on either side.

1. Charming 1-bedroom apartment in downtown Westminster along Main Street

Charming 1-bedroom apartment in downtown Westminster along Main Street
Westminster
$245 nightly
The price is $259
Nov 10 - Nov 11
Total with taxes and fees
Charming 1-bedroom apartment in downtown Westminster along Main Street
A brick entrance with a dark wooden door, a small set of steps, and two signs indicating the address '68 W. Main'.

2. Cozy 1-bedroom apartment in downtown Westminster along Main Street

Cozy 1-bedroom apartment in downtown Westminster along Main Street
Westminster
$245 nightly
The price is $259
Nov 10 - Nov 11
Total with taxes and fees
Cozy 1-bedroom apartment in downtown Westminster along Main Street
A wooden deck with a fire pit, outdoor furniture, and string lights.

3. 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.
$442 nightly
The price is $468
Nov 8 - Nov 9
Total with taxes and fees
Paws, Pizza & Patio | Private Oasis Westminster
A bedroom with a large bed, a wooden nightstand, a chair, and a view of the outdoors through a window.

4. Adorable 1-bedroom apartment in downtown Westminster along Main Street

Adorable 1-bedroom apartment in downtown Westminster along Main Street
Westminster
$201 nightly
The price is $213
Nov 10 - Nov 11
Total with taxes and fees
Adorable 1-bedroom apartment in downtown Westminster along Main Street
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

5. 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.
$384 nightly
The price is $407
Nov 13 - Nov 14
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-Site!
A sunroom with a wicker chair, a wooden chest, and a view through large glass doors.

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
$408 nightly
The price is $432
Nov 13 - Nov 14
Total with taxes and fees
Rural & Historic Detour Escape w/ Horses On-site!
A wooden staircase with metal railings leading to a covered area surrounded by greenery.

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

The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
Westminster
$172 nightly
The price is $183
Nov 10 - Nov 11
Total with taxes and fees
The Whimsy Loft-Cozy Private Suite in Westminster on 4 acres
A living room with a fireplace, two sofas, a patterned rug, and framed artwork on the walls.

8. 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.
$344 nightly
The price is $364
Nov 9 - Nov 10
Total with taxes and fees
Private Sauna, Fireplace and Country Views
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.
$238 nightly
The price is $264
Nov 8 - Nov 9
Total with taxes and fees
Charming 1-bedroom cottage with AC, WiFi in downtown Hanover, PA
Living area

10. Cozy studio charming Hanover

Cozy studio charming Hanover
Hanover
8.8 out of 10, Excellent, (15 reviews)
"Place was as described. "
United States
Katie F.
$123 nightly
The price is $136
Nov 8 - Nov 9
Total with taxes and fees
Cozy studio charming Hanover
A covered patio area with outdoor furniture, a grill, and a stone wall.

11. Hot Tub Farmhouse | Near Gettysburg | Sleeps 11

Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
Littlestown
10.0 out of 10, Exceptional, (23 reviews)
"We loved the quiet location, and while the house felt wonderfully quaint, it was beautifully updated inside. The space was incredibly clean and the kitchen had everything we needed. Highly recommended if you want to relax!"
United States
Carolyn W.
$718 nightly
The price is $808
Nov 15 - Nov 16
Total with taxes and fees
Hot Tub Farmhouse | Near Gettysburg | Sleeps 11
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

12. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (107 reviews)
"Great location"
United States
John
$295 nightly
The price is $312
Nov 9 - Nov 10
Total with taxes and fees
Modern Condo Right off Market Street
A ping pong table in a room with a television, a plant, and a sofa.

13. 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.
$132 nightly
The price is $140
Nov 8 - Nov 9
Total with taxes and fees
Charming studio with 1 queen sofa bed and 1 full bath . With AC, WiFi and TV
A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

14. 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, (18 reviews)
"Place was perfect and tbe location great. East in and out town..or to get to down town"
United States
Andrew
$215 nightly
The price is $228
Nov 22 - Nov 23
Total with taxes and fees
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
A modern kitchen with dark cabinets, a large island with stools, a stainless steel refrigerator, and a built-in oven.

15. 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.
$433 nightly
The price is $459
Nov 8 - Nov 9
Total with taxes and fees
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.

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

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (72 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.
$256 nightly
The price is $272
Nov 10 - Nov 11
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A cozy living room with a ceiling fan, a black leather sofa, a coffee table, and a wooden ladder.

17. 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.
$187 nightly
The price is $216
Nov 8 - Nov 9
Total with taxes and fees
Cozy Guesthouse in Woodstock, MD
A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

18. 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.
$363 nightly
The price is $385
Nov 9 - Nov 10
Total with taxes and fees
New townhouse
A modern kitchen with grey cabinets, a central island, and pendant lighting.

19. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (102 reviews)
"Very convenient location with parking. Prompt communication with owner. However it needs a good deep clean. My towels were used and muddy like the workmen fixing the deck had just showered there. But I would stay there again if necessary."
United States
Jessica
$305 nightly
The price is $323
Nov 8 - Nov 9
Total with taxes and fees
Luxury Condo In Downtown Frederick
Property grounds

20. Entire lower level furnished home

Entire lower level furnished home
Owings Mills
2.0 out of 10, (2 reviews)
"Our reservation was cancelled because the owner never provided check in instructions, never responded to messages or phone calls. Drove almost to the house when VRBO office staff was able to help us. We were stranded! Definitely not a reputable owner!!! Stay clear of this property!"
United States
Megan K. K.
$227 nightly
The price is $262
Nov 8 - Nov 9
Total with taxes and fees
Entire lower level furnished home
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

A spacious living room with a central fireplace, large windows, and a view of the outside.
Best Western Westminster Hotel

Best Western Westminster Hotel

Best Western Westminster Hotel
Westminster

10/10 Excellent

Nice, quiet hotel near the college and easy to find. The bathroom only had a shower instead of a tub, and I had hoped to soak away the road-weariness in a nice bath, but everything else was top-notch. Quiet hours begin at 10 p.m., which we weary travelers appreciated after many hours on the road in heavy traffic. The room was clean, the beds were comfortable, and the free breakfast was outstanding. In addition to the usual self-serve options, there was also a chef who cooked eggs and...
United States
Mary
Reviewed November 24, 2016
Best Western Westminster Hotel

Find out more about New Windsor

Everything you need to know about New Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $133 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Windsor rentals

At Expedia, we put the best New Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.