Apartment holiday rentals in Western Maryland

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Top-rated apartment rentals in Western Maryland

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

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Guest favourite

Flat in Cumberland

4.95 out of 5 average rating, 109 reviews

The Dove's Nest w/no cleaning fees

The Dove's Nest features a fully equipped chefs kitchen , dishwasher, washer and dryer, plenty of parking and a large private patio with bike parking. Easily accessible from I-68 and ideally located in a comfortable part of town. Less than 1 mile from the University of Pittsburgh Medical Center (UPMC), Allegany College of MD and the Constitution Park. A quick 2 miles to historic downtown Cumberland where the C & O Canal meets the Great Allegheny Passage. Perfect location for hiking and biking.

Guest favourite

Flat in Winchester

5.0 out of 5 average rating, 142 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

Flat in Winchester

4.98 out of 5 average rating, 218 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 favourite

Flat in Winchester

4.94 out of 5 average rating, 276 reviews

Downtown 1920's Gas Station

Luxury 1920’s Refurbished Gas Station repurposed into a beautiful apartment. Private off-street parking/EV car charging station, full kitchen, custom shower with rain system, super high speed wifi, smart TV & Blu-Ray. Plenty of light with frosted garaged doors. AC/Heat, Washer/Dryer, Dish Washer, coffee nook, and open living design. Be a part of Old Town Winchester in this unique fun space in walking distance to breweries, neighborhood Pizzoco Pizza parlor and the downtown walking mall.

Guest favourite

Flat in Cumberland

4.99 out of 5 average rating, 334 reviews

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

Guest favourite

Flat in The Plains

4.98 out of 5 average rating, 455 reviews

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Guest favourite

Flat in Shepherdstown

4.94 out of 5 average rating, 207 reviews

Charming Studio Apt in Downtown Shepherdstown

Live like a local in our newly renovated, studio apartment in the heart of downtown Shepherdstown. Comfortably blending modern conveniences with historic charm, the 2nd floor studio apartment – which features space for no more than 2 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.

Guest favourite

Flat in Shepherdstown

4.97 out of 5 average rating, 156 reviews

Downtown Luxe Apt: Pet Friendly & Fenced Courtyard

Welcome to our warm and modern one-bedroom apartment, just steps away from history, dining, the great outdoors, and Shepherd University campus! Enjoy the convenience of street front access while enjoying a clean and private space away from the downtown bustle. Additionally, we offer a large shared fenced-in courtyard, providing a secure and spacious area for your furry friend to play. This is the perfect place to relax and unwind, and experience the historic charm of Shepherdstown.

Guest favourite

Flat in Shepherdstown

4.91 out of 5 average rating, 141 reviews

Downtown Modern Studio apartment | History & Dining steps away

Welcome to our modern studio, just steps away from the vibrant heart of Shepherdstown. Whether for a relaxing weekend escape or a university visit, our cozy apartment offers an ideal oasis with a comfortable queen bed, dedicated work area, and walk-in shower. Nestled in downtown Shepherdstown, easily explore downtown, and discover a wide variety of dining options, shopping, and recreational activities, all while being a short walk away from the Potomac River.

Guest favourite

Flat in Bruceton Mills

4.99 out of 5 average rating, 380 reviews

Coopers Rock Retreat

Industrial farmhouse studio apartment nestled in the hills of West Virginia. Located just 15 minutes to downtown Morgantown and only 5 short minutes away from Coopers Rock State Forest. Spectacular landscape views from dusk to dawn and breathtaking star gazing once the sun has set. Guests will have their own private entrance to come and go as they please and full kitchenette to make home cooked meals while on the road. Check out our IG@coopersrockretreat!

Guest favourite

Flat in Shepherdstown

4.98 out of 5 average rating, 122 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!

Guest favourite

Flat in Bedford

4.96 out of 5 average rating, 268 reviews

Spacious & Private 2-Bedroom Apartment

Spacious newly renovated 1500 sq. ft. 2-bedroom apartment in private setting. Conveniently located along Business 220 two miles from the Pennsylvania Turnpike and I-99, 7 minutes from route 30, and 5 miles from downtown Bedford, PA. Located in the rear of a warehouse occupied by a non-profit. 2 bedrooms with queen size beds. Roku TV (no cable or local channels) & DVD player. Full kitchen, laundry & bath.