Apartment holiday rentals in Frederick County

A cozy kitchen features a brick accent wall and a vintage clock. The space includes a gas stove and an under-counter sink, with warm light provided by string lights along the window. A white kitchen cart and various utensils are neatly arranged for guest use.

4.88 out of 5 average rating, 224 reviews

Nostalgia Lane 3 BR in the heart of the city

Steps from the Walking Mall this 2nd floor apartment is in a vintage Tudor style building overlooking the downtown city street. Its space is light & airy full of charm & it’s spacious-3 bedrooms will make for a fabulous stay. You can park & spend your time enjoying the local breweries the iconic John Handley Library, the Discovery Museum, delicious restaurants, galleries & shops just outside your door. Nostalgia Lane has a wonderfully peaceful relaxing vibe —You will love it ! Happy Travels!

A spacious living area features a stylish black leather sofa adorned with a shearling throw. Behind it, an artistic wall is covered in colorful vinyl records. A coffee table with a glass top sits on a vibrant area rug, complementing the eclectic design.

4.94 out of 5 average rating, 183 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!

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.

4.91 out of 5 average rating, 386 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!

4.82 out of 5 average rating, 17 reviews

Magnolia Wind 3 BR 1 BA loft… walk to downtown.

If you are coming to Winchester and you want to stay in an elegant renovated loft just steps from the iconic John Handley library and the downtown walking mall… then this is the spot. Hardwood floors, floor to ceiling windows all the charm that a building built in the 1900’s exudes. Guests will enjoy the fully stocked kitchen, comfortable king size bed, as well as a queen bed room with desk /a sleeping porch with two twins /and pull out sofa bed in the loft for extra guests. You will love it!

Apartment in Berkeley Springs

An open-concept kitchen, dining, and living area is highlighted by original hardwood floors. Natural light fills the space through dual windows, showcasing a dining table adjacent to a breakfast nook. The kitchen has modern appliances, and a cozy seating area is complemented by framed nature artwork on the walls.

5 out of 5 average rating, 19 reviews

"Over The Ridge" Vintage Modern Apartment

"Over The Ridge" is a historic 1860's vintage modern private apartment with no one above or below you! SMOKE FREE! Located on the main route to Berkeley Springs and just minutes from Cacapon Resort State Park, this two-bedroom apartment features a separate entrance, original hardwood floors, spa-like bathroom, and curated modern design. Free parking and in-unit laundry are available. Set above a future coffee house, this stay offers history and contemporary style in one unforgettable space.

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.

5 out of 5 average rating, 240 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.

A spacious dining area features a wooden table with woven placemats, surrounded by upholstered chairs. Natural light fills the room through the windows. A comfortable seating arrangement with a sofa is visible in the background, complemented by a television on a console.

4.97 out of 5 average rating, 319 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.

5 out of 5 average rating, 7 reviews

The room features two spacious beds, one made with a white coverlet. A wooden dresser and open closet provide storage. Light filters through the blinds of the windows, and red accent walls are complemented by framed artwork depicting a cow.

Apartment in Inwood

Traveling Professional and Tourist Suite

You will feel right at home in this ground floor apartment located close to two main hospitals, P&G, Amazon, Clorox and more. If you're not here to work, you will enjoy local historical civil war sites, national parks, beautiful rivers and all West Virginia has to offer in the Eastern Panhandle. Backpack through Harpers Ferry, explore the Appalachian Trail, visit the local farm markets, go antique shopping or visit a local festival-- You will love it here! West Virginia- Wild and Wonderful!

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.

4.94 out of 5 average rating, 17 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 living area features a comfortable green sofa set and a beige recliner. A large flat-screen TV is positioned across from the seating. Soft lighting is provided by two table lamps. Two glass doors lead to the outside, with a patterned rug anchoring the space.

5 out of 5 average rating, 19 reviews

Lovely 1100 Sq. ft. 1 bedroom basement apartment

Forget your worries in this large serene space. We are conveniently located 10 minutes west of Winchester and the Medical Center and about 15 minutes from downtown. Enjoy the basement apartment which is closed off from the rest of the house so you will be left undisturbed. You have a private entrance with key code so you may come and go as you please. This is a perfect place for those temporarily working in Winchester or nearby. We look forward to hosting your stay!

Apartment in Berkeley County

5 out of 5 average rating, 11 reviews

Private basement unit Bunker Hill, WV (WV-VA line)

Forget your worries in this private, fully furnished, spacious unit located on the WV-VA line. Follow a lighted paver path to the side gate into your own sub fence leading to the basement unit. The unit has a dorm refrigerator, microwave and 2 burner portable induction cook top for anyone wanting to cook. Our home is 5mins off of Interstate 81 and from the Amazon distribution center. We are approximately 20mins to Winchester, VA and 20mins to Martinsburg, WV.