Apartment vacation rentals in Frederick County

A cozy living area features a light beige couch paired with a plush armchair in soft gray. A decorative area rug with intricate patterns lies under a glass table. Natural light filters through a window with yellow curtains, illuminating the space.

4.91 out of 5 average rating, 11 reviews

Retro Loves Company in Old Town Winchester

Spacious, light-filled apartment nestled in a beautiful, historic, well-established, safe neighborhood. Excellent location just 2 blocks from Old Town Winchester pedestrian mall with shops, restaurants, cafes & entertainment. High speed internet & everything you need. The medical rehab center is walking distance, the Winchester Medical Center (Hospital) a 5-minute drive & Shenandoah University is less than 8 minutes away. The apartment is on the top 3rd floor of 1840s house with quiet neighbors

A spacious living area features a stylish black leather sofa adorned with a shearling throw. Behind it, an artistic wall is covered in colorful vinyl records. A coffee table with a glass top sits on a vibrant area rug, complementing the eclectic design.

4.93 out of 5 average rating, 155 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!

An open living area features a modern kitchenette with a sleek countertop and bar stools. A cozy seating nook with vibrant yellow accents invites relaxation, while natural light streams through the large window and door, enhancing the welcoming atmosphere.

4.91 out of 5 average rating, 343 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!

A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.

5 out of 5 average rating, 202 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.

A cozy living area features two light brown sofas adorned with colorful throw pillows. A glass-top coffee table is centered between them. Sunlight filters through the large windows, which are framed by light-colored curtains, creating a bright and inviting space.

4.97 out of 5 average rating, 273 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.

Guest favorite

A cozy dining area features a wooden table with two placemats and a potted plant centerpiece. Light streaming through large windows is diffused by floral-patterned curtains, illuminating a comfortable sofa and two wooden chairs nearby. Decorative artwork hangs on the wall, adding character to the space.

4.8 out of 5 average rating, 294 reviews

Pretty Little Apt by the Train II

This little place is just plain charming. Lots of light and personality. Wonderful alternative to the typical hotel experience. Fabulous for short term rental needs. Come enjoy Downtown Flat screen TV/ Record Player FREE PARKING/WIFI Near Piccadillys Pub, the Walking Mall, our beautiful and historic library, Shenandoah Univ. -5 minute Winchester Med Center -5 min DC. -1.5 hr Skyline Drive -30 min Free Parking too ! Reach out on social media if you need more. Michele Bouve Hoffman

A spacious bedroom is highlighted by large bay windows with blue curtains. A dark wood bed frames a neatly made bed, complemented by a decorative table and elegant furniture pieces. A ceiling fan is mounted above, providing a comfortable ambiance.

4.67 out of 5 average rating, 33 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 favorite

A comfortable sitting area is illuminated by natural light filtering through sheer curtains. A floral-patterned couch is paired with a wooden side table, featuring a small decorative arrangement. Artwork depicting floral themes adorns the wall, complementing the elegant drapery.

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!

A spacious one-room suite features a memory foam queen bed and a wooden bunk bed, suitable for children. Two comfortable armchairs and a small table provide additional seating. A small television is mounted on the wall, and a private entrance is visible, allowing easy access.

5 out of 5 average rating, 42 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!

Apartment in Stephens City

A cozy sitting area features a tan sofa adorned with decorative pillows in vibrant colors. Above, two floral artworks enhance the wall. A circular glass coffee table sits in front, accompanied by coffee cups, adding to the inviting atmosphere of the space.

4.83 out of 5 average rating, 6 reviews

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.

Apartment in Stephens City

A vibrant red sofa is positioned in the living area, adorned with patterned throw pillows and a knitted blanket. Two floor lamps provide warm lighting, enhancing the cozy ambiance. A low black coffee table sits in front, with a decorative tray placed on top.

5 out of 5 average rating, 16 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!

A light-filled living area is decorated in soft pink hues, featuring a mounted television on the wall. Two gray upholstered seating areas are positioned for comfort. Hardwood flooring adds warmth to the space, complemented by natural light filtering through nearby windows.