Holiday Rentals in Frederick County

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Our top choices for Frederick County holiday rentals

Property grounds
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

Luxury tiny home farm stay on historic property with hot tub in Stephens City
2.0 star property
Stephens City
10.0 out of 10, Exceptional, (1)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is €143
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Interior
Rosamond nice downtown studio apt

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2)
"Small but appropriately priced."
United States
John M.
The price is €168
includes taxes & fees
1 Jan - 2 Jan 2026
Rosamond nice downtown studio apt
Fridge, microwave, oven, stovetop
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

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

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
Winchester Historic District
8.6 out of 10, Excellent, (4)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Fridge, microwave, oven, stovetop
Cameron Charmer pristine downtown apt with double master suites

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)
"Nice house in a good central location. "
United States
Mitchell V.
The price is €306
includes taxes & fees
29 Dec - 30 Dec
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop
The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
Winchester Historic District
6.0 out of 10, (1)
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop
The Little Red Schoolhouse

The Little Red Schoolhouse

The Little Red Schoolhouse
Cross Junction
9.8 out of 10, Exceptional, (13)
"We loved the overall school house theme. Very comfortable accommodations! "
United States
Tony Z.
The price is €174
includes taxes & fees
21 Jan - 22 Jan 2026
The Little Red Schoolhouse
3 bedrooms, iron/ironing board, WiFi, bed sheets
Nostalgia Lane in the heart of the city

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, (14)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is €288
includes taxes & fees
28 Dec - 29 Dec
Nostalgia Lane in the heart of the city
Dining
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

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, (6)
"Indigo Blue is in a beautiful neighborhood and we loved the house and location!"
United States
Tricia M.
The price is €325
includes taxes & fees
29 Dec - 30 Dec
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Microwave, oven, stovetop, dishwasher
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

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1)
"Beautiful space; helpful host."
United States
Sally C.
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Terrace/patio
Scarborough Fair walk to downtown two story apt

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, (5)
"Charming home! Lovely decor. Was perfect for our stay. Great location, walkable to the historical district. Host was very friendly and communicative. "
United States
Stephanie L.
Scarborough Fair walk to downtown two story apt
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (66)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is €93
includes taxes & fees
5 Jan - 6 Jan 2026
❤️ Secluded 1940s Romantic Tiny House on the River
Fridge, microwave, coffee/tea maker, dining tables
Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (5)
"Cozy, beautiful, pretty new and well-maintained cabins. Very inviting outdoor seating area with fire pit and grill on the grounds. There is a (very small) grocery store within walking distance. Highly recommend the short drive to Zumbrun Overlook to watch the sunset - it's unforgettable! The cabins are located in a quiet and very small town (although you can hear the highway traffic in the distance). Nice drive to Little Orleans (to get on the C&O Canal towpath). The host was super responsive....
United States
W L.
The price is €140
includes taxes & fees
4 Jan - 5 Jan 2026
Private cabin with two double beds (sleep 4)
Outdoor dining
Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet

Primitive Cozy Tiny Cabin with Starlink internet
Great Cacapon
10.0 out of 10, Exceptional, (11)
"Super peaceful and relaxing! We had a great time! Will stay again! Thanks Austin!"
United States
Jason M.
The price is €162
includes taxes & fees
6 Jan - 7 Jan 2026
Primitive Cozy Tiny Cabin with Starlink internet
Exterior
2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
9.4 out of 10, Exceptional, (3)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is €237
includes taxes & fees
5 Jan - 6 Jan 2026
2-Bedroom cabin Hot tub Fireplace PS5
Smart TV, stereo
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets
Fort Valley
9.8 out of 10, Exceptional, (55)
"It was a beautiful getaway from all of the busy mess from our normal lives"
United States
Tailor N.
The price is €236
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Retreat - Hot tub + Mountain Views + Pets
Fridge, microwave, oven, stovetop
Peaceful Retreat on Creekside

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.6 out of 10, Exceptional, (15)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is €183
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful Retreat on Creekside
Fridge, microwave, oven, stovetop
Upscale w Fireplace, Fire Pit, Games in Gated Comm

Upscale w Fireplace, Fire Pit, Games in Gated Comm

Upscale w Fireplace, Fire Pit, Games in Gated Comm
2.0 star property
Paw Paw
9.6 out of 10, Exceptional, (5)
"The cabin was so detailed it blew me away amazing place to stay very relaxing and very secluded "
United States
Frank
The price is €310
includes taxes & fees
4 Jan - 5 Jan 2026
Upscale w Fireplace, Fire Pit, Games in Gated Comm
Outdoor spa tub
Lookout Cabin in the mountains, Amazing Views!

Lookout Cabin in the mountains, Amazing Views!

Lookout Cabin in the mountains, Amazing Views!
Page County
10.0 out of 10, Exceptional, (31)
"Nice view! And hot tub! "
United States
Lauren E.
The price is €340
includes taxes & fees
19 Jan - 20 Jan 2026
Lookout Cabin in the mountains, Amazing Views!
Fridge, microwave, oven, stovetop
Oldtown Guesthouse

Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (29)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is €157
includes taxes & fees
31 Dec - 1 Jan 2026
Oldtown Guesthouse
3 bedrooms, free WiFi, bed sheets
Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (13)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is €364
includes taxes & fees
11 Jan - 12 Jan 2026
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.
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Top Frederick County Hotel Reviews

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Room was clean and no bad smells. Enjoyed the hard boiled egg at breakfast. "
Helene 1-night trip
Posted 4 days ago
Hampton Inn Martinsburg

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Holiday Homes in Frederick County

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