Apartment vacation 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 favorite

Apartment 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.

Sep 21 – 28

$84 per night

Guest favorite

Apartment in Capon Bridge

4.99 out of 5 average rating, 116 reviews

Paw Paw Suite ~ 1 of 5 Unique Stays at Basswood

For those seeking to step away from the bustle of the city and slow down in a friendly, charming town. Basswood is a historic home that has been lovingly remodeled to include five private suites each with their own unique style. The Paw Paw Suite is an inviting space with a queen size bed, double shower bathroom, and kitchenette. Located in the heart of Capon Bridge, you'll find it easy to walk to everything. For a relaxing stay in a friendly, artsy community, this is a great place to enjoy.

Dec 21 – 28

$69 per night

Guest favorite

Apartment in Winchester

5.0 out of 5 average rating, 139 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.

Jul 31 – Aug 7

$144 per night

Guest favorite

Apartment 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.

Oct 6 – 13

$98 per night

Guest favorite

Apartment in Cumberland

4.84 out of 5 average rating, 295 reviews

WOW! Rustic-Modern Apt - PETS WELCOME!

Quaint and comfy one bedroom apartment located just one block from historic downtown cumberland. It is in a safe and quiet neighborhood. The Cumberland Theatre & Western Maryland Scenic Railroad, the C&O Canal and GAP Trail are just around the corner. We are pet friendly (one-time per pet fee applies, billed after booking) but we do a deep clean after each guest, you’d never know that pets have ever been hosted. AT THIS TIME, WE ARE UNABLE TO ACCOMMODATE EARLY CHECK-IN/OUT DUE TO COVID.

May 31 – Jun 7

$70 per night

Guest favorite

Apartment in Winchester

4.94 out of 5 average rating, 273 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.

Nov 28 – Dec 5

$122 per night

Guest favorite

Apartment in Cumberland

4.99 out of 5 average rating, 327 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.

Mar 3 – 10

$86 per night

Guest favorite

Apartment in Shepherdstown

4.95 out of 5 average rating, 202 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.

Feb 8 – 15

$99 per night

Guest favorite

Apartment in Shenandoah Junction

4.91 out of 5 average rating, 188 reviews

Private apt near Shepherdstown

A Little Respite is our private 1 bedroom apt *King size bed *Queen size pullout sofa *7 min from Shepherdstown, 15 min from Harpers Ferry *self check-in *full kitchen *fast Wi-Fi & Roku channels *magnetic chargers *Alexa alarm clock/sound machine *quiet *fire-pit and gas grill *ideal rustic family retreat *getaway for outdoor enthusiasts, bikers, hikers, and paddlers *remote work & business traveler friendly *2 miles from Marc commuter train *Weekly and monthly stays welcome

Jul 9 – 16

$79 per night

Guest favorite

Apartment in The Plains

4.98 out of 5 average rating, 451 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.

Oct 7 – 14

$77 per night

Guest favorite

Apartment 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.

Jun 30 – Jul 7

$132 per night

Guest favorite

Apartment in Bruceton Mills

4.99 out of 5 average rating, 376 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!

Aug 12 – 19

$100 per night