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

TV

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
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$1,160
HK$2,051 total
includes taxes & fees
30 Aug - 31 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Interior

2. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location for walking around Old Town Winchester!"
United States
Clint B.
The price is HK$1,019
HK$1,732 total
includes taxes & fees
3 Sept - 4 Sept
Pretty Little Apt by the Train II
Interior

3. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is HK$862
HK$1,519 total
includes taxes & fees
30 Aug - 31 Aug
Rosamond nice downtown studio apt
Exterior detail

4. 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 HK$862
HK$1,572 total
includes taxes & fees
30 Aug - 31 Aug
The Stock Exchange downtown 3rd floor studio apt
Terrace/patio

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, (13 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$1,448 total
includes taxes & fees
31 Aug - 1 Sept
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Smart TV, fireplace, video games, DVD player

6. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (86 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
The price is HK$980
HK$2,643 total
includes taxes & fees
16 Sept - 17 Sept
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Smart TV, books

7. 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 HK$1,082
HK$1,803 total
includes taxes & fees
31 Aug - 1 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Coffee/tea maker, fridge, stovetop, lobster pot

8. Buena Vista

Buena Vista
Shawneeland
The price is HK$682
HK$1,701 total
includes taxes & fees
9 Sept - 10 Sept
Buena Vista
Smart TV

9. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
Yellow Submarine trendy basement apt and courtyard
Living area

10. 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$1,395
HK$2,567 total
includes taxes & fees
14 Sept - 15 Sept
Morocco Loft 2BR overlooking city walking mall
Private kitchen

11. 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$1,326
HK$2,586 total
includes taxes & fees
31 Aug - 1 Sept
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Smart TV

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, (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$1,450
HK$2,620 total
includes taxes & fees
3 Sept - 4 Sept
Nostalgia Lane in the heart of the city
Private kitchen

13. 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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,529
HK$1,980 total
includes taxes & fees
31 Aug - 1 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Exterior

14. 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$1,552
HK$2,762 total
includes taxes & fees
30 Aug - 31 Aug
Cameron Charmer pristine downtown apt with double master suites
Dining

15. 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$1,607
HK$2,931 total
includes taxes & fees
30 Aug - 31 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Interior

16. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is HK$1,724
HK$3,179 total
includes taxes & fees
30 Aug - 31 Aug
Indigo Blue modern open vibe on tree lined street
Smart TV, fireplace

17. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is HK$1,740
HK$3,100 total
includes taxes & fees
30 Aug - 31 Aug
Scarborough Fair walk to downtown two story apt
Pillow-top beds, free WiFi, bed sheets

18. 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$1,113
HK$1,258 total
includes taxes & fees
29 Aug - 30 Aug
Canal Cabins
Dining

19. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (23 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is HK$941
HK$1,744 total
includes taxes & fees
1 Sept - 2 Sept
Quaint Mini Cottage in Shepherdstown - Walking Distance
Exterior

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
The price is HK$508
HK$1,042 total
includes taxes & fees
7 Sept - 8 Sept
❤️ Secluded 1940s Romantic Tiny House on the River
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"No"
Diane 1-night trip
Posted 16 hours ago
Quality Inn Winchester