Holiday houses in Frederick County

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Top-rated holiday rentals in Frederick County

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Top Guest favourite

An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.

Cottage in Winchester

COZY+SEXY Private Country Escape! HOT TUB & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

4.99 out of 5 average rating, 492 reviews

Top Guest favourite

The modern ranch home features a two-story design with a wide front staircase leading to the upper porch. The exterior is painted in neutral tones and is surrounded by green grass and trees, with a clear blue sky visible overhead.

Home in Winchester

Swim, kayak, fish, and enjoy nature on Back Creek

Classic Georgian home in the Shenandoah Valley with cherry wood floors and french chandeliers. Six acres of pristine, waterfront privacy just 20 minutes from downtown Winchester. There are 3 bedrooms (1 king bed and 2 queen beds) and 3 bathrooms. Upstairs, there is an open-concept living area with a full kitchen, pantry and laundry room. Downstairs, there is a regulation pool table, dart board, reclining sofa, and workspace with PC and printer. The front porch has a sweeping view of Back Creek.

4.93 out of 5 average rating, 60 reviews

Top Guest favourite

Tiny home in Stephens City

Farm Stay in a luxury tiny home with hot tub

Welcome to “Horsefeathers” a tiny home on an historic property where you will be immersed in a farm experience! Although tiny, this house is equipped with all top of the line luxuries to include a personal hot tub, an automatic cappuccino maker, a king nectar mattress-just to name a few. Only minutes to Winchester the location is convenient to restaurants and shopping yet you’ll feel like you have been transported back in time to a working homestead where you can interact with all the animals.

5.0 out of 5 average rating, 164 reviews

Guest favourite

The cabin is illuminated at night, showcasing its rustic charm among surrounding trees. Warm lights accentuate the porch and pathway, enhancing the inviting atmosphere. The outdoor space is highlighted by well-placed rocks and greenery, creating a serene outdoor retreat.

Home in High View

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fish~Swim

Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a heavy forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

4.95 out of 5 average rating, 181 reviews

Top Guest favourite

A cozy living space features a wooden ceiling and light-colored walls. A small electric fireplace is placed beneath a wall-mounted television. A coffee table sits centrally, surrounded by two comfortable chairs and a couch, with a front door visible to the side.

Cabin in High View

Mary's Cabin

Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

4.98 out of 5 average rating, 209 reviews

Top Guest favourite

The exterior of the cabin is showcased, featuring large vaulted windows that allow natural light to fill the space. The deck is furnished with a table and chairs, surrounded by a lush yard and trees displaying autumn colors.

Cabin in Gerrardstown

The Nest: Modern Cabin Retreat on 5 Wooded Acres

Welcome to The Nest, a light‑filled, chalet‑style cabin tucked into 5 wooded acres. A short drive from Berkeley Springs, Harpers Ferry, and Cacapon State Park, it’s your base for hot springs, hiking, trails, and small‑town restaurants. By day, explore paths, wineries, and historic main streets. By night, come “home” to star‑studded skies, mountain views, and wildlife. With fast Wi‑Fi, a workspace, and a fully stocked kitchen, The Nest is perfect for families, couples, and remote workers.

4.98 out of 5 average rating, 209 reviews

Guest favourite

Loft in Winchester

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

4.74 out of 5 average rating, 737 reviews

Top Guest favourite

The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.

Home in Winchester

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

4.97 out of 5 average rating, 294 reviews

Top Guest favourite

Cottage in Capon Bridge

River Front Retreat *HotTub-FirePit-Kayaks*

Unplug and unwind. *River Front *Steps away from Cacapon River with easy access *Hot tub facing river *Kayaks with Life vests on property *Decks with BBQ and dining Alfresco *Two Fire pits: River Front Wood Fire pit and Propane on the Deck *Yard games/board games *Wi-Fi and Smart TV. *Comfy beds/black out curtains *Pet-Friendly ($25/day for 2 dogs) ***pet policy below Come step into nature and nurture your spirit at our riverfront haven.

5.0 out of 5 average rating, 110 reviews

Guest favourite

A modern cabin exterior is shown, featuring a sloped roof and large windows that allow natural light to fill the interior. A spacious deck is visible, furnished with two lounge chairs and a wooden rocking chair, surrounded by vibrant autumn foliage.

Cabin in Winchester

Foxtrot Mokki | Secluded Getaway 2 Hours from DC

Welcome to The Foxtrot Mokki—a Nordic-inspired retreat just two hours from DC and Baltimore. Solitude is signature. Nestled on seven secluded acres with rain-fed streams, our cozy cabin is designed for tranquility and connection with nature. Located between Old Town Winchester, VA, and Berkeley Springs, WV, it's the perfect outpost for exploring the Northern Shenandoah Valley—from charming towns to scenic hikes and wineries.

4.96 out of 5 average rating, 179 reviews

Guest favourite

A private hot tub is positioned on a wooden deck, surrounded by trees and greenery. The view of the distant landscape is visible, with soft colors of nature reflecting a serene atmosphere. Soft lighting fixtures hang from the roof, adding to the inviting space.

Cabin in Gerrardstown

Modern Eclectic Treetop Cabin ~ Hottub ~ Romantic

Our cabin in the treetops is the perfect place to rest, work remotely, or use as a basecamp for exploring the surrounding area. The cabin has many modern conveniences including an eco-friendly hot tub with epic views, high speed internet and chromecast for streaming your connected devices. Hot tub is available year round and safe for max of 2 adults due to its location on the upper deck. Pellet stove is available Oct-March.

4.9 out of 5 average rating, 248 reviews

Top Guest favourite

A two-story farmhouse is surrounded by well-maintained greenery, featuring a white exterior with a green roof. An American flag is displayed on the front porch, which is complemented by a wide entrance. Large windows allow ample natural light into the home.

Home in Winchester

Aunt Tim's Farmhouse

Our farmhouse is located approximately 5 miles west of Historic Winchester, VA. The house is situated on 106 acres of an operational farm. You may see family members and friends tending honey bee hives, working in the detached garage, gardening, and completing other farm chores. The house is solely occupied by our guests. Come on out to enjoy some peace and quiet and take advantage of all Mother Nature has to offer!

4.96 out of 5 average rating, 163 reviews