A building with a green roof and ornate architectural details.

Frederick County 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

Top Cities in Frederick County

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.
Vacation RentalsVacation Rentals

Winchester

Winchester

Our top choices for Frederick County vacation rentals

A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

1. 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 CA $156
CA $276 total
includes taxes & fees
Oct 6 - Oct 7
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. 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 CA $107
CA $356 total
includes taxes & fees
Oct 5 - Oct 6
The Queen of Winchester Three Bedroom with Upper Level Deck
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

3. 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
10.0 out of 10, Exceptional, (2 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 CA $211
CA $371 total
includes taxes & fees
Oct 4 - Oct 5
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

4. 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 CA $196
CA $332 total
includes taxes & fees
Oct 4 - Oct 5
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A hot tub in front of a wooden cabin with a tree in the background.

5. 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, (14 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is CA $206
CA $261 total
includes taxes & fees
Oct 6 - Oct 7
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a sofa, ottoman, lamp, and a mirror.

6. 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 CA $228
CA $431 total
includes taxes & fees
Oct 4 - Oct 5
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

7. 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, (13 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is CA $277
CA $355 total
includes taxes & fees
Oct 4 - Oct 5
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A two-story house with a front porch, a mailbox, and a number plate.

8. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 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 CA $282
CA $503 total
includes taxes & fees
Oct 7 - Oct 8
Cameron Charmer pristine downtown apt with double master suites
A white building with a black door and a set of blue-painted stairs with black railings.

9. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is CA $164
CA $274 total
includes taxes & fees
Oct 4 - Oct 5
The Blue Door steps from Handley Library
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

10. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is CA $241
CA $464 total
includes taxes & fees
Oct 10 - Oct 11
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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 CA $147
CA $335 total
includes taxes & fees
Oct 6 - Oct 7
Buena Vista
A living room with a sofa, armchair, coffee table, and a television.

12. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (19 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 CA $263
CA $477 total
includes taxes & fees
Oct 4 - Oct 5
Nostalgia Lane in the heart of the city
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

13. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is CA $316
CA $564 total
includes taxes & fees
Oct 4 - Oct 5
Scarborough Fair walk to downtown two story apt
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

14. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
The price is CA $292
CA $532 total
includes taxes & fees
Oct 4 - Oct 5
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A bed with a dark quilted cover, two beige pillows, and a headboard with two wall-mounted lamps.

15. Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (17 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
The price is CA $194
CA $219 total
includes taxes & fees
Oct 5 - Oct 6
Canal Cabins
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is CA $65
CA $159 total
includes taxes & fees
Oct 15 - Oct 16
❤️ Secluded 1940s Romantic Tiny House on the River
A wooden deck with white railings and a covered porch area.

17. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (43 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is CA $192
CA $312 total
includes taxes & fees
Oct 4 - Oct 5
Mountain View Bungalow in Front Royal
A living room with a dining table, chairs, a sofa, and a television.

18. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is CA $213
CA $372 total
includes taxes & fees
Oct 18 - Oct 19
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious room with a large dining table, white chairs, and a ceiling fan.

19. ~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, (106 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is CA $238
CA $518 total
includes taxes & fees
Oct 6 - Oct 7
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A wooden deck with a hot tub, outdoor seating, and string lights.

20. Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
10.0 out of 10, Exceptional, (44 reviews)
"Great place, perfect for a getaway"
United States
Cindy T.
The price is CA $131
CA $420 total
includes taxes & fees
Oct 5 - Oct 6
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
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 Frederick County Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

8/10 Good
"Well sized clean room with comfortable, hot showers and large fridge. Well, engineered room layout from electrical connections to lighting and HVAC controls but wished fridge had freezer option."
Lisa 1-night trip
Posted 18 hours ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Frederick County

Everything you need to know about Frederick County 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 Frederick County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Frederick County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Frederick County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Frederick County vacation rentals we have selected for you start as low as CA $159 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 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 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 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 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.