New Windsor Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

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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

Westminster

$245 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Westminster

$245 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

3. Paws, Pizza & Patio | Private Oasis Westminster

Westminster

Payson D.

$442 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Westminster

$201 nightly

Nov 10 - Nov 11

Total with taxes and fees

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!

Detour

Mary F.

$384 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

Keymar

$408 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

Westminster

$172 nightly

Nov 10 - Nov 11

Total with taxes and fees

A living room with a fireplace, two sofas, a patterned rug, and framed artwork on the walls.

8. Private Sauna, Fireplace and Country Views

Mount Airy

Richard B.

$344 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Hanover

Danna W.

$238 nightly

Nov 8 - Nov 9

Total with taxes and fees

10. Cozy studio charming Hanover

Hanover

Katie F.

$123 nightly

Nov 8 - Nov 9

Total with taxes and fees

A covered patio area with outdoor furniture, a grill, and a stone wall.

11. Hot Tub Farmhouse | Near Gettysburg | Sleeps 11

Littlestown

Carolyn W.

$718 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

12. Modern Condo Right off Market Street

Downtown Frederick

John

$294 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

Woodbine

Scott C.

$132 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Frederick

Andrew

$215 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

Frederick

Janice M.

$433 nightly

Nov 8 - Nov 9

Total with taxes and fees

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)

Frederick

Sara W.

$256 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Woodstock

Marie E M.

$187 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with a granite countertop, stainless steel appliances, and a white backsplash.

18. New townhouse

Frederick

Tereasa G.

$363 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with grey cabinets, a central island, and pendant lighting.

19. Luxury Condo In Downtown Frederick

Downtown Frederick

Jessica

$304 nightly

Nov 10 - Nov 11

Total with taxes and fees

20. Entire lower level furnished home

Owings Mills

Megan K. K.

$227 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top New Windsor Hotel Reviews

A deck with outdoor seating and string lights.

Sunday Morning at Savannahs

New Windsor

10/10 Excellent

We had a girls night here. Everything was excellent. It was a beautiful facility. It has lots of charming character. You feel like you have simply left home and went to stay at your grandmother's house, which is a very good thing In my book I felt right at home. When we arrived there were snacks and fresh baked chocolate chip cookies water The owner was very accommodating and pleasant. Everything was great. Food and accommodations highly recommend. Definitely plan to go back

CRYSTAL

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

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...

Mary

Days Inn by Wyndham Westminster

Westminster

10/10 Excellent

Fazeela

An indoor swimming pool with clear water, surrounded by lounge chairs and a mural of autumn trees.

Best Western Gettysburg

Gettysburg Historic District

10/10 Excellent

Jerome

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.

SpringHill Suites by Marriott Frederick

Frederick

10/10 Excellent

Anonymous traveler

A Holiday Inn Express & Suites with a covered entrance and stone pillars.

Holiday Inn Express and Suites Gettysburg by IHG

Gettysburg

10/10 Excellent

Riyah

A spacious living area with a large sectional sofa, a coffee table, and a staircase with a railing.

Marriott Owings Mills Metro Centre

Owings Mills

10/10 Excellent

LaKeisha

A spacious living area with a staircase, a sofa set, a coffee table, and a bookshelf.

Inn at Cemetery Hill

Gettysburg Historic District

10/10 Excellent

Jill

A Hampton Inn & Suites hotel with a modern facade, large columns, and a well-lit entrance.

Hampton Inn & Suites Frederick-Fort Detrick

Frederick

10/10 Excellent

Anonymous traveler

A two-story house with a porch and a staircase leading to the front door.

Hollerstown Hill Bed and Breakfast

Frederick

10/10 Excellent

Yvette

An outdoor patio area with yellow chairs, a fire pit, and a row of sofas with striped cushions.

Home2 Suites by Hilton Owings Mills

Owings Mills

10/10 Excellent

Timaira

A hotel room with a kitchenette, a dining area with a round table and chairs, and a large window.

Hampton Inn Hanover

Hanover

10/10 Excellent

Karla

A spacious lobby with a high ceiling, a central pillar, and a seating area with a blue sofa.

Comfort Suites Near Gettysburg Battlefield Visitor Center

Gettysburg Historic District

10/10 Excellent

Breakfast area and spacious rooms are worth the stay here. We were unknowingly there during Bike Week. The employees were clearly a little worn out from all the travelers coming through, but still professional and nice. Despite how many people there were. Somehow there was always easy access to the luggage carts and plenty of food & seating options for breakfast. And the parking lot was easy to get in and out of.

Cheyenne

An outdoor patio with a circular fire pit, wicker furniture, and a grill area.

Residence Inn by Marriott Baltimore Owings Mills

Owings Mills

10/10 Excellent

Igor

A large house with a stone facade and a covered porch, set against a sunset sky.

The Lodges at Gettysburg

Gettysburg

10/10 Excellent

dana

A modern urban plaza with a central roundabout, surrounded by multi-story buildings with commercial establishments.

Holiday Inn Express & Suites Owings Mills-Baltimore Area by IHG

Owings Mills

10/10 Excellent

Leida

A white house with a porch, a garden with daisies, and a black planter.

Inn at Mary's Land Farm

Clarksville

10/10 Excellent

Margaret

A Holiday Inn Express building with a covered entrance and a visible parking lot.

Holiday Inn Express Hanover by IHG

Hanover

10/10 Excellent

Anonymous traveler

A circular outdoor seating area with a fire pit, surrounded by chairs and tables, set on a brick patio with trees in the background.

TownePlace Suites by Marriott Frederick

Frederick

10/10 Excellent

Mikael

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.