Apartment vacation rentals in Frederick County

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!

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!

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!

"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.

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!

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.

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!

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!

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.