Frederick County Holiday 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

Top cities in Frederick County

A white neoclassical building with columns, an American flag, and a clock tower.
Vacation Rentals

Winchester

Winchester

Check prices for these dates

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

Our top choices for Frederick County holiday rentals

A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

1. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is AU$362
includes taxes & fees
1 Dec - 2 Dec
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

2. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (17 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A living room with a sofa, ottoman, lamp, and a mirror.

3. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is AU$440
includes taxes & fees
18 Nov - 19 Nov
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

4. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is AU$347
includes taxes & fees
30 Nov - 1 Dec
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

5. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is AU$267
includes taxes & fees
15 Nov - 16 Nov
Rosamond nice downtown studio apt
A two-story house with a front porch, a mailbox, and a number plate.

6. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is AU$468
includes taxes & fees
8 Nov - 9 Nov
Cameron Charmer pristine downtown apt with double master suites
A hot tub in front of a wooden cabin with a tree in the background.

7. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is AU$254
includes taxes & fees
16 Nov - 17 Nov
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

8. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.4 out of 10, Very good, (6 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is AU$326
includes taxes & fees
15 Nov - 16 Nov
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a sofa, armchair, coffee table, and a television.

9. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is AU$447
includes taxes & fees
8 Nov - 9 Nov
Nostalgia Lane in the heart of the city
A building with a red door, white trim, and a small balcony with a metal railing.

10. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is AU$279
includes taxes & fees
12 Nov - 13 Nov
The Stock Exchange downtown 3rd floor studio apt
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

11. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is AU$277
includes taxes & fees
8 Dec - 9 Dec
Buena Vista
A wooden deck with white railings and a covered porch area.

12. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (49 reviews)
"Very cute and clean home. The location was great and Vanessa was awesome to work with"
United States
Diedra
The price is AU$297
includes taxes & fees
9 Nov - 10 Nov
Mountain View Bungalow in Front Royal
A garden with a wooden swing set and a circular seating area.

13. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (57 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is AU$443
includes taxes & fees
29 Nov - 30 Nov
Newly renovated Farm cottage with Mountain views
A room with a large window, a round table, and two chairs.

14. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (112 reviews)
"Absolutely charming cabin - clean, comfortable and with lovely amenities."
United States
Diane S.
The price is AU$421
includes taxes & fees
1 Dec - 2 Dec
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

15. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A hot tub with a view of a forest and a sunset.

16. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is AU$449
includes taxes & fees
17 Nov - 18 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A living room with a dining table, chairs, a sofa, and a television.

17. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is AU$329
includes taxes & fees
9 Nov - 10 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a large window, a wooden coffee table, and a sofa.

18. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$449
includes taxes & fees
9 Nov - 10 Nov
Schilling House
A sunroom with a large glass wall, a dining table set for four, and a ceiling fan.

19. Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful, well managed property. Quiet lake, rustic log cabin feel with modern amenities."
United States
Andrew A.
The price is AU$629
includes taxes & fees
11 Nov - 12 Nov
Log Cabin w/ Hot Tub & Waterfront Patio!
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

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Find out more about Frederick County

Everything you need to know about Frederick County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Frederick County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Frederick County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Frederick County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Frederick County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Frederick County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Frederick County holiday rentals we have chosen for you start as low as AU$253 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Frederick County rentals

At Expedia, we put the best Frederick County holiday 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 Frederick County 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 Frederick County holiday.

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