Apartment holiday rentals in Frederick County

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!

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!

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.

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!

The Flat of Old Town Winchester

Stylish and cozy, this unique flat is your perfect downtown Winchester escape. Located in the heart of Old Town, you're just steps from the historic walking mall, shops, restaurants, and local entertainment. The flat features a comfy living space with an electric fireplace, wall-mounted TV, and a well-equipped kitchenette with a fridge, microwave, coffee maker, and silverware—everything you need for a relaxing stay.

"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!

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.