Apartment holiday rentals in Frederick County

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!

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!

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.

Home Away from Home

Are you a professional? Traveling nurse? An occupational, physical, speech or music therapist? Looking for a short-term Lease with lots of charm in an excellent locatiom? We're nestled in a beautiful, historic, safe neighborhood within walking distance to the quaint Winchester downtown area. The medical rehabilitation center in a 10 minute walk and the Winchester Medical Center Hospital is a 6 minute drive. The apartment is on the 3rd floor walk-up of a historic 1840s home with parking.

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!

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.

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!

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..