A building with a green roof and ornate architectural details.

Frederick County Holiday Rentals

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Our top choices for Frederick County holiday rentals

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

1. 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 HK$659
HK$1,949 total
includes taxes & fees
30 Sept - 1 Oct
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.

2. 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 HK$1,161
HK$1,982 total
includes taxes & fees
30 Sept - 1 Oct
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

3. 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 HK$863
HK$1,511 total
includes taxes & fees
30 Sept - 1 Oct
Rosamond nice downtown studio apt
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)
The price is HK$1,082
HK$1,804 total
includes taxes & fees
11 Oct - 12 Oct
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 HK$1,137
HK$1,441 total
includes taxes & fees
4 Oct - 5 Oct
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

6. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is HK$737
HK$1,696 total
includes taxes & fees
30 Sept - 1 Oct
Buena Vista
A white building with a black door and a set of blue-painted stairs with black railings.

7. 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 HK$902
HK$1,511 total
includes taxes & fees
11 Oct - 12 Oct
The Blue Door steps from Handley Library
A living room with a sofa, ottoman, lamp, and a mirror.

8. 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 HK$1,396
HK$2,426 total
includes taxes & fees
14 Oct - 15 Oct
Morocco Loft 2BR overlooking city 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
9.2 out of 10, Wonderful, (18 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 HK$1,451
HK$2,488 total
includes taxes & fees
11 Oct - 12 Oct
Nostalgia Lane in the heart of the city
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

10. 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, (12 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is HK$1,530
HK$1,911 total
includes taxes & fees
11 Oct - 12 Oct
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.

11. 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 HK$1,553
HK$2,604 total
includes taxes & fees
29 Oct - 30 Oct
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

12. 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 HK$1,742
HK$2,906 total
includes taxes & fees
30 Sept - 1 Oct
Scarborough Fair walk to downtown two story apt
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

13. 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 HK$1,475
HK$2,604 total
includes taxes & fees
27 Oct - 28 Oct
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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 HK$1,608
HK$2,755 total
includes taxes & fees
11 Oct - 12 Oct
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 HK$1,114
HK$1,259 total
includes taxes & fees
2 Oct - 3 Oct
Canal Cabins
A small attic bedroom with a sloped ceiling, a single bed, and a window.

16. Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
9.4 out of 10, Exceptional, (14 reviews)
"Always a great stay. Peaceful and plenty to explore. We cant wait to come back!"
United States
Anthony A.
The price is HK$607
HK$1,505 total
includes taxes & fees
30 Sept - 1 Oct
Primitive Cozy Tiny Cabin with Starlink internet
A garden with a wooden swing set and a circular seating area.

17. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (51 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 HK$1,130
HK$2,284 total
includes taxes & fees
5 Oct - 6 Oct
Newly renovated Farm cottage with Mountain views
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 HK$941
HK$1,704 total
includes taxes & fees
1 Oct - 2 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A hot tub with a view of a forest and a sunset.

19. 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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden deck with white railings and a covered porch area.

20. 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 HK$1,059
HK$1,702 total
includes taxes & fees
5 Oct - 6 Oct
Mountain View Bungalow in Front Royal
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 Frederick County Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Top notch hotel! We had a great stay. Shelby was awesome and very helpful!"
Erik 1-night trip
Posted 1 hour ago
Microtel Inn & Suites by Wyndham Winchester