Apartment holiday rentals in Frederick County

The Comfortable In-Towner

A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

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 !

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!

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!

"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.

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!

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.

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.

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!

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!

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!

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!