Apartment vacation rentals in Frederick County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Frederick County

Guests agree: these apartments are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

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.

Apartment in Winchester

4.99 out of 5 average rating, 76 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 !

Guest favorite

A living area features a neutral-colored sofa and an accent chair with a decorative cushion. A glass coffee table is centered on a vibrant area rug, with a plant placed on top. A flat-screen television is mounted on the wall, providing a cozy space for relaxation.

Apartment in Winchester

4.91 out of 5 average rating, 22 reviews

Retro Loves Company in Old Town Winchester

Spacious, light-filled apartment nestled in a beautiful, historic, well-established, safe neighborhood. Excellent location just 2 blocks from Old Town Winchester pedestrian mall with shops, restaurants, cafes & entertainment. High speed internet & everything you need. The medical rehab center is walking distance, the Winchester Medical Center (Hospital) a 5-minute drive & Shenandoah University is less than 8 minutes away. The apartment is on the top 3rd floor of 1840s house with quiet neighbors

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.

Apartment in Winchester

4.9 out of 5 average rating, 364 reviews

Old Town 1920s Gas Station with Hot Tub

1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, 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, laundry and coffee nook in 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!

Top guest favorite

Aerial view captures the historic downtown Winchester at sunset, with buildings showcasing varied architectural styles. The warm glow of the sun illuminates the skyline, highlighting the rooftops and the distinctive features of the surroundings. Streets lined with trees provide a scenic backdrop.

Apartment in Winchester

4.89 out of 5 average rating, 237 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

Top guest favorite

A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.

Apartment in Winchester

5 out of 5 average rating, 223 reviews

Old Town Loft In Highly Desirable Area Downtown

Location, Location! A completely renovated apartment in the highly desirable center 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 reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.

Top guest favorite

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.

Apartment in Winchester

4.97 out of 5 average rating, 299 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.

Top guest favorite

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.

Apartment in Winchester

4.91 out of 5 average rating, 117 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.

Top guest favorite

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.

Apartment in Winchester

5 out of 5 average rating, 54 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!

Superhost

A cozy sitting area is illustrated with two floral paintings on light green walls. A beige sofa is adorned with colorful pillows in shades of orange and green. A sleek black lamp is positioned beside the sofa, providing focused lighting, while a small table holds decorative items.

Apartment in Stephens City

4.88 out of 5 average rating, 8 reviews

Newtown Cozy Cottage Basement

Keep it simple at this peaceful and centrally-located brand new apartment. Enjoy a walk or run in the quiet neighborhood. Minutes away from Rt.11, Rt. 81 and Rt. 37. Also minutes from shops, delicious restaurants, wineries, and one of the few remaining drive-in movie theaters in the country. Historic downtown Winchester is only minutes away. Nearby national parks and historic sites offer endless possibilities. Take a day trip to DC- less than 2 hours away.

Top guest favorite

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.

Apartment in Stephens City

5 out of 5 average rating, 18 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 spacious living room features a large sectional sofa designed for comfort, complemented by decorative pillows. A neutral area rug lies beneath, and several framed photos adorn the wall, while a smart TV is mounted opposite, with natural light accessible through a nearby door.

Apartment in Winchester

5 out of 5 average rating, 3 reviews

Apt c/ Movie Theater Pool Table Treadmill.

Here our accommodation is special because it provides a cozy space where you can share beautiful moments. We offer a home theater for enjoying movies with family and friends. Additionally, guests can indulge in entertainment with the pool table, air hockey and ping pong table. For those who enjoy staying active, there's a treadmill available. These amenities are designed to ensure your stay is both memorable and fun-filled..

Guest favorite

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.

Apartment in Winchester

4.91 out of 5 average rating, 113 reviews

Newly repurposed Historic Home in Winchester VA!

The historic “Homespun” is located on the border between Frederick County and the city of Winchester. Originally built in the mid 1790’s the Homespun is significant in local architecture as an example of a dogtrot-plan structure, a rare building form of this period. The property is listed on the National register of Historic Places and Virginia Landmark Registry.