Apartment vacation rentals in Frederick County

A tire swing hangs from a tree, with sunlight filtering through the branches, casting rays across the grassy yard. The background offers a view of distant hills and trees, creating a serene outdoor space ideal for relaxation.

4.99 out of 5 average rating, 74 reviews

Merrimans Meadow

Come to a beautiful tucked away spot where you can relax and unwind. You will absolutely love Merrimans Meadow; a spacious studio with beautiful sunsets and views of the mountains. This welcoming English Basement has lots of light, lovely furnishings, tasteful decor, and a varied collection of original acrylic and watercolor paintings. Nearby: 1/2 mile to Winchester Medical Ctr. 1 m Downtown Winchester, 4m to Shenandoah University Explore DC 1.5 hr Skyline Drive 20 m Local history abounds !

A vibrant wall adorned with a collage of classic album covers captures attention, showcasing a blend of colors and styles. In the foreground, a sleek glass coffee table rests on polished hardwood floors, accompanied by a plush red chair, contributing to a stylish and artistic ambiance.

4.93 out of 5 average rating, 161 reviews

Modern Twist in Old Town! Rock n' Roll FUN!

Basil is your personal, 2 bedroom, Uber-stylish apartment, located in downtown Winchester with private parking! New & sparkling clean, enjoy high end finishes & creative design! Enjoy hot showers in the marble bath, sink into the shearling-covered couch relaxing in front of the new 55' smart TV, catch up with work in your private office, then walk to a great happy hour & dinner downtown! End your day cozying up in one of the two queen size, memory foam canopy beds! Basil is your perfect Airbnb!

Superhost

A contemporary building with a mix of stone and modern gray walls is showcased, featuring large glass windows and wooden accents. A bright yellow door provides a pop of color at the entrance. The surrounding area includes wooden railings and landscaped greenery.

4.9 out of 5 average rating, 357 reviews

Downtown 1920's Gas Station with Hot Tub

Luxury 1920’s Refurbished Gas Station and hot tub repurposed into a beautiful apartment. Private parking/EV charging station, private hot tub, full kitchen, custom rain shower, high speed wifi, and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, coffee nook, and an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

A cozy living area features two light brown sofas adorned with colorful throw pillows. A glass-top coffee table is centered between them. Sunlight filters through the large windows, which are framed by light-colored curtains, creating a bright and inviting space.

4.97 out of 5 average rating, 285 reviews

Downtowner

No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

A cozy living area is furnished with a sofa and an accent chair, positioned around a coffee table. A warm fireplace complements the space, while a dining area with a table and chairs is visible in the background. Soft lighting enhances the inviting ambiance.

4.91 out of 5 average rating, 112 reviews

Scarborough Fair walk to downtown two story apt

Come to downtown Winchester get the true feel of the city. Park & Walk to beautiful Handley Library, take a stroll to the much loved walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three bedrooms, two levels, three porches, fenced yard. Eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? or have any additional questions? Reach out on social media: Michele Bouve Hoffman.

The living area features a spacious sectional sofa positioned around a round coffee table. A soft area rug lies beneath. Natural light filters through multiple windows with blinds, illuminating the hardwood floors. A decorative plant adds a touch of greenery, while a lamp provides warm lighting.

4.98 out of 5 average rating, 109 reviews

Old Town Loft Modern Oasis In Downtown Winchester

Location, Location! A completely renovated, 2 bed/1 bath, 1100 sq. ft. apt in the highly desirable center of Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, memory foam mattresses, high speed Wi-Fi, 60’ smart TV, Xfinity HDTV, AC/Heat, Washer/Dryer, dishwasher and 2 free parking spaces.

A comfortable sitting area is illuminated by natural light filtering through sheer curtains. A floral-patterned couch is paired with a wooden side table, featuring a small decorative arrangement. Artwork depicting floral themes adorns the wall, complementing the elegant drapery.

4.93 out of 5 average rating, 15 reviews

Cameron Grace brand new downtown 1 BR loft

Stunning brand new 1 BR apt within walking distance to everything downtown. Meticulously maintained and beautifully decorated. Full of light and plenty of space to live and work. The apt is overtop of the garage in the rear of another established Airbnb. Designated Free driveway parking spot just steps up to your own private oasis overlooking the treetops. Whether you plan to stay for a night, a week or longer this private relaxing spot will not disappoint! You will LOVE it!

A spacious one-room suite features a memory foam queen bed and a wooden bunk bed, suitable for children. Two comfortable armchairs and a small table provide additional seating. A small television is mounted on the wall, and a private entrance is visible, allowing easy access.

5 out of 5 average rating, 47 reviews

Peaceful Family Retreat in the Heart of Winchester

Come relax in our beautiful one-room basement suite. The suite is closed off from the rest of the house so you and your family will be undisturbed. A private entrance with your own custom keycode means you can come and go as you please. Rest easy on our memory foam queen bed. The kids will enjoy the bunk bed and plenty of board games for entertainment. Roam around our quiet neighborhood or drive just a short distance to shops and entertainment. We can't wait to host you!

Apartment in Stephens City

A cozy living area features a red sofa adorned with decorative pillows, facing a wooden media console with a television. A round coffee table sits centrally on a patterned rug. Two lamps provide soft lighting, creating an inviting space for relaxation.

5 out of 5 average rating, 16 reviews

Spacious Charming Basement Apt

This newly renovated space with private entrance is perfect for traveling professionals and vacation travelers alike. Close proximity to shopping and restaurants. Just off Main St (Rt 11), it is convenient to Rts 37 and 81. Less than 15 minute drive to Winchester Medical Center, Shenandoah University. Visit Local Wineries/Family Drive In Theater/ Harpers Ferry/ Skyline Drive/ Historic Winchester/ Take a day trip to DC- just 1.5 hours away. Options abound!

Superhost

A modern living area features a gray tufted sofa complemented by decorative pillows. Two vibrant abstract artworks hang on the white walls. A glass dining table with four chairs is positioned nearby, with warm wood flooring enhancing the inviting atmosphere of the space.

4.77 out of 5 average rating, 13 reviews

"Cozy on Cameron!" - Historic Downtown Winchester

Welcome to our chic 1BR, 1B downtown gem in Winchester! Ideal for urban explorers, steps away from the charming walking mall lined with shops & eateries, you find the apartment is complete with a modern kitchenette, smart TV in the living room, workspace desk in the bedroom, a marble-laced bathroom, and an exclusive off-street parking spot. Perfect for a cozy stay in this vibrant area - schedule your arrival today!

A light-filled living area features a cream-colored sofa with yellow accent pillows and a patterned ottoman. A dining table with chairs is visible in the background, along with a large window allowing natural light to illuminate the space.

4.95 out of 5 average rating, 77 reviews

Easy like a Sunday Morning 1 BR apt great location

You will enjoy easy access to everything from this centrally located apartment. Comfortable, easy-going yet stylish, light-filled apartment on the 2nd floor of a historic 1840s home with terrific neighbors just two short-walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, coffee cafes, museums, entertainment, breweries and wine bars.

The exterior of a historic building is showcased, displaying a combination of red and blue painted sections alongside stone walls. Traditional windows with shutters complement the architecture. Flags are positioned by the entrance, and a pathway lined with grass leads to the entrance.