Apartment holiday rentals in Frederick County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Frederick County

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Guest favourite

Rental unit

4.91 out of 5 average rating, 196 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!

Guest favourite

Rental unit

4.92 out of 5 average rating, 137 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!

Guest favourite

Rental unit

4.92 out of 5 average rating, 310 reviews

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!

Guest favourite

Rental unit

5 out of 5 average rating, 178 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.

Guest favourite

Rental unit

4.97 out of 5 average rating, 251 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.

Superhost

Rental unit

4.69 out of 5 average rating, 26 reviews

The Flat of Old Town Winchester

This unique Flat has a style all its own. This Flat is the perfect get away! Enjoy downtown Winchester! Walk the historic walking mall and enjoy one of the great restaurants located there. This apartment has a small kitchenette with a microwave, refrigerator, coffee maker, silverware and everything you need to be comfortable. It also has electric fireplace and Tv mounted on wall. Located in the heart of Old Town Winchester. Walking distance to shops, restaurants, and entertainment.

Guest favourite

Rental unit

4.92 out of 5 average rating, 13 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!

Guest favourite

Rental unit

5 out of 5 average rating, 5 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!

Guest favourite

Rental unit

5 out of 5 average rating, 39 reviews

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!

Guest favourite

Rental unit

5 out of 5 average rating, 13 reviews

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!

Guest favourite

Rental unit

5 out of 5 average rating, 7 reviews

The Queen of Winchester - Three Bedroom Apartment

Nestled in the picturesque city of Winchester, the "Queen of Winchester" offers a tranquil escape in a prime location that perfectly blends convenience and comfort. This beautifully renovated three-bedroom apartment is situated on the upper level with a terrace deck, promising privacy and views of the surrounding area. Whether you're visiting for a relaxing retreat or a business trip, this property is designed to ensure a memorable and luxurious stay.