Frederick County Holiday Rentals

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Our top choices for Frederick County holiday rentals

Terrace/patio

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, (4 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is HK$1,135
HK$1,406 total
includes taxes & fees
27 Apr - 28 Apr
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Interior

Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is HK$1,018
HK$1,686 total
includes taxes & fees
13 Apr - 14 Apr
Pretty Little Apt by the Train II
Fridge, microwave, oven, stovetop

The Little Red Schoolhouse

The Little Red Schoolhouse
Cross Junction
9.8 out of 10, Exceptional, (14 reviews)
"Lovely two night stay. The hot tub was clean and enjoyable as quick get away for my husband and me. Would absolutely stay again and refer others to do the same. "
United States
Nikki B.
The Little Red Schoolhouse
Interior

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$861
HK$1,508 total
includes taxes & fees
13 Apr - 14 Apr
Rosamond nice downtown studio apt
Smart TV

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (16 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is HK$1,449
HK$2,582 total
includes taxes & fees
13 Apr - 14 Apr
Nostalgia Lane in the heart of the city
Living area

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is HK$1,394
HK$2,484 total
includes taxes & fees
19 Apr - 20 Apr
Morocco Loft 2BR overlooking city walking mall
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is HK$1,551
HK$2,768 total
includes taxes & fees
10 May - 11 May
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 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$783
HK$1,650 total
includes taxes & fees
13 Apr - 14 Apr
The Queen of Winchester Three Bedroom with Upper Level Deck
Interior

Very charming & spacious 2 bedrm

Very charming & spacious 2 bedrm
Winchester
The price is HK$550
HK$1,195 total
includes taxes & fees
26 Apr - 27 Apr
Very charming & spacious 2 bedrm
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
6.0 out of 10, (1 review)
The price is HK$861
HK$1,553 total
includes taxes & fees
3 May - 4 May
The Stock Exchange downtown 3rd floor studio apt
Smart TV, books

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
8.6 out of 10, Excellent, (4 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is HK$1,081
HK$1,801 total
includes taxes & fees
13 Apr - 14 Apr
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV

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.
The price is HK$1,143
HK$1,996 total
includes taxes & fees
13 Apr - 14 Apr
Yellow Submarine trendy basement apt and courtyard
Dining

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
9.2 out of 10, Wonderful, (7 reviews)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is HK$1,605
HK$2,901 total
includes taxes & fees
15 Apr - 16 Apr
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Smart TV, fireplace

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, (6 reviews)
"Excellent location, easy walk to most of the Old Town area. Michele is a great host, will definitely stay here again if in the area. "
United States
Larry E.
The price is HK$1,738
HK$3,070 total
includes taxes & fees
13 Apr - 14 Apr
Scarborough Fair walk to downtown two story apt
Interior

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,723
HK$3,052 total
includes taxes & fees
13 Apr - 14 Apr
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Pillow-top beds, free WiFi, bed sheets

Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.6 out of 10, Exceptional, (14 reviews)
"Great place for bikers to stay"
United States
mark
The price is HK$1,056
HK$1,194 total
includes taxes & fees
17 Apr - 18 Apr
Canal Cabins
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (73 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is HK$507
HK$1,041 total
includes taxes & fees
20 Apr - 21 Apr
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Berkeley Springs
9.0 out of 10, Wonderful, (19 reviews)
"Hot tub was nice relaxing cozy cabin"
United States
kristin
The price is HK$514
HK$1,444 total
includes taxes & fees
14 Apr - 15 Apr
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill
Property grounds

Charming Cottage on 15 Acre Farm near Romney, WV

Charming Cottage on 15 Acre Farm near Romney, WV
Romney
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was wonderful. We enjoyed everything; very clean, neat and had anything we could need. The communication was good. We enjoyed the breakfast and snack items and the fire pit and front porch…highly recommend."
United States
Doris H.
The price is HK$1,096
HK$1,464 total
includes taxes & fees
13 Apr - 14 Apr
Charming Cottage on 15 Acre Farm near Romney, WV
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.6 out of 10, Excellent, (4 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is HK$1,263
HK$2,200 total
includes taxes & fees
13 Apr - 14 Apr
2-Bedroom cabin Hot tub Fireplace PS5
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

8/10 Good
"It was a short stay- probably 15 min. Because we were not where we thought we should be- the receptionist was very nice and shared she’d need to speak to a me aged to clear it up since we’d taken possession of the keys. Which is fine- hoping to find some resolution with that sometimes soon"
Morgan 1-night trip
Posted 11 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG