Apartment vacation rentals in Greencastle

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Greencastle

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A compact kitchen area features modern appliances, including a microwave and small refrigerator, along with a sink. Two stylish bar stools are positioned at a countertop. The space opens into a well-lit living area, with the bedroom visible in the background.

Apartment in Downtown Frederick

4.93 out of 5 average rating, 102 reviews

Charming Historic Downtown Apartment…The Fox’s Den

Guests will love this beautifully renovated downtown apartment, which features all the modern amenities while retaining its historic charm! Over 1,650 square feet of living area and a large outdoor deck off the master bedroom to enjoy in the warmer months. Walking distance to the wonderful downtown Frederick shops and restaurants and the award winning Carroll Creek Linear Park (don't miss the holiday-themed boats during the winter months) and only a short drive to hiking, parks and wineries!

Top guest favorite

The exterior of a spacious two-story house is presented, featuring a light brown façade, large windows, and decorative window shutters. A welcoming front porch is visible, adorned with potted greenery. A driveway leads to a closed garage, with a basketball hoop positioned nearby.

Apartment in Germantown

4.93 out of 5 average rating, 102 reviews

Private/Cozy Lower Level Apt-Great for Long Stays

Private entrance to One-bedroom apartment with Queen Bed, Full Bath, Lounge, Kitchenette/Dinette and Pool/Billiard Room. Perks include Wifi, Cable TV, Air-conditioning & Heating, Keurig Coffee Maker, Toaster, Microwave and Refrigerator, Hair Dryer, and Iron with Ironing board. Awesome safe neighborhood on a cul-de-sac, great landscape with a quiet & serene backyard facing wild life conservation land blending into Seneca Park trail. Perfect for a jog, or just read, and watch the deer and birds.

Top guest favorite

A bright living space features two turquoise chairs with decorative cushions, positioned on warm hardwood flooring. A small plant rests on a white side table, while a well-appointed kitchenette with light wood cabinetry is visible in the background. Natural light streams through the windows.

Apartment in Downtown Frederick

4.99 out of 5 average rating, 152 reviews

Carroll Creek Private Apt./Luxury King Bed

Within footsteps to Carroll Creek Promenade offering easy access to posh restaurants, fun Breweries, local shops and festivals galore! Modern remodel and furniture including a posh memory foam king bed. Enjoy your own apartment w/ wide open spaces & high ceilings that bring in fantastic light. Historic bldg. (circa 1840) with all the modern appointments to make your stay super comfortable and fun! Owners provide advice on their favorite places and restaurants! Easy self checkin. Free parking.

Top guest favorite

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.

Apartment in Winchester

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.

Superhost

A bright living area is showcased with a comfortable seating arrangement, including a dark sofa and a pair of accent chairs. A dining table with six chairs sits nearby, while a television is positioned across the room. Natural light filters through the windows, enhancing the airy feel.

Apartment in Harpers Ferry

4.79 out of 5 average rating, 141 reviews

Best location! The Pullman Apt @ historic 1799 Inn

Immerse yourself in rich history while you relax in your comfy, one-bedroom apartment with kitchenette in the 2nd oldest building in town. The perfect location if you're cycling the C&O, hiking the AT, or coming by train. And you'll be just steps from historic Lower Town Harpers Ferry. The Harpers Ferry train station is just across the street. A 2-minute walk brings you to the scenic confluence of the Potomac and Shenandoah rivers as well as Harpers Ferry National Park and John Browns Fort.

Top guest favorite

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.

Apartment in Winchester

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.

Apartment in Winchester

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

Guest favorite

A cozy living area features a blue sofa accentuated with decorative pillows and a glass coffee table. Natural light enters through two windowpanes, illuminating a colorful area rug that adds warmth. A subtle lamp stands beside the sofa, providing additional light for relaxation.

Apartment in Shepherdstown

4.96 out of 5 average rating, 137 reviews

Downtown Modern 2BR step from dining and shopping

Welcome to a modern and conveniently located two-bedroom apartment in the heart of Shepherdstown. Whether you're planning a weekend getaway or visiting the university, this apartment offers a perfect escape for your trip. Inside, you'll find a thoughtfully designed space with a coffee bar, a cozy living room, a versatile work/play room, high-speed internet, and a state-of-the-art kitchen. Explore downtown and discover a wide variety of dining options, shopping, and recreation activities.

Guest favorite

A cozy living room features a modern gray couch and a dark accent wall decorated with two framed art pieces. A light area rug adds warmth to the wooden floor. Natural light filters through sheer curtains on a window, and a coffee table sits in front of the couch.

Apartment in Shepherdstown

4.94 out of 5 average rating, 323 reviews

1 Bedroom Apt in Historic Downtown Shepherdstown

Live like a local in our newly renovated, one-bedroom apartment in the heart of downtown Shepherdstown. Comfortably blending modern conveniences with historic charm, the 2nd floor apartment – which features space for no more than 3 guests – is located in a 100-year-old building directly behind Shepherd University's campus on German Street. Walk to the town’s restaurants, shops, and the university during Theater season, sporting events, or graduation. Comes with one free parking space

Superhost

A cozy living room is showcased with a gray sofa adorned with patterned throw pillows. Two lamps with decorative bases provide warm lighting on either side, complemented by a wooden coffee table positioned in the center. A rug adds texture to the space.

Apartment in Berkeley Springs

4.88 out of 5 average rating, 107 reviews

1 Bedroom Apartment in Downtown Berkeley Springs

LOCATION! Enjoy easy access to everything from this perfectly located second floor apartment. This cozy apartment is a wonderful home away from home featuring many amenities. Separate Bedroom with Queen bed and walk-in closet Living Room with loveseat, chair, tv, end tables, coffee table, sofa table Free parking WiFi Full Kitchen with appliances, dishes, utensils, pots and pans Keurig Coffee Toaster Table and Chairs Bath with Single shower Washer and Dryer Small Porch Sitting Area

Top guest favorite

A cozy sleeping area features a spacious bed dressed in white bedding with a red patterned throw. Nightstands with lamps are positioned on either side of the bed. Windows allow natural light to brighten the room, and a ceiling fan is mounted overhead.

Apartment in Gettysburg

4.98 out of 5 average rating, 101 reviews

Rebel Hollow

Come stay with us for the ultimate battlefield experience! The 1920s Farmhouse on six wooded acres on Willoughby Run directly across the street from the Herbst Woods where the first day's infantry battle occurred on July 1st, 1863. It is hard to get much closer, with less than a 2 minute drive to the battlefield and a 4 minute drive to historic downtown Gettysburg. We are also just over a 10 minute drive to Liberty Ski Resort with ample parking!

Top guest favorite

A bright room is illuminated by natural light from three windows adorned with potted plants. A wooden desk with matching chairs is positioned between the windows, complemented by a vintage record player on a side table. A decorative mirror and a cozy basket add to the inviting atmosphere.

Apartment in Shepherdstown

4.98 out of 5 average rating, 181 reviews

The 1763 House - Stay in Downtown Shepherdstown

Welcome to our charming downtown Shepherdstown apartment, originally built in 1763 and nestled in the heart of town. Ideal for getaways, visiting family/friends, or university trips. Enjoy a spacious interior, comfortable living room, state-of-the-art kitchen, and private patio. Our downtown location on the Main Street offers convenient access to a wide selection of restaurants, unique shopping, and the Potomac river, all just a short walk away!