Vacation rentals in Shepherdstown

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Top-rated vacation rentals in Shepherdstown

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 568 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Guest favorite

Guest suite in Shepherdstown

4.99 out of 5 average rating, 210 reviews

Private Suite in Shepherdstown WV

Your sun-drenched suite awaits in my serene bungalow! Self check-in with keypad lock through your separate driveway and entrance. Free parking in front. Private porch with seating and table overlooking the garden. Walk downtown in five minutes to all that Shepherdstown has to offer - Shepherd University, restaurants, shopping, pubs, and theatre. Close by- the C&O Canal Towpath, Potomac River, Harper's Ferry, and Antietam National Battlefields. Bikers, hikers, and kayakers especially welcome!

Guest favorite

Treehouse in Shepherdstown

4.97 out of 5 average rating, 250 reviews

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Superhost

Home in Shepherdstown

4.8 out of 5 average rating, 128 reviews

Plum Lazy on the Potomac

With stunning views and prime river access, Plum Lazy is nestled on three partially-wooded acres sloping gently to the water's edge. Enjoy 150 feet of shoreline with a large landscaped expanse of grass perfect for play, picnics, or just shady naps. This riverfront area is exclusively for you and guests at our cabin on Knott Road. A rocky peninsula extends your riverfront another 100 feet into the Potomac. The large deck and stone patio features a variety of seating options and gas grill.

Guest favorite

Apartment in Shepherdstown

4.95 out of 5 average rating, 203 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 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.

Guest favorite

Home in Shepherdstown

4.94 out of 5 average rating, 215 reviews

Small Town Living: Historic District Guesthouse

The Michael Yeasley guest house is a charming way station tucked in downtown Shepherdstown, the oldest enclave in West Virginia and one teeming with restaurants, coffee shops and arts and crafts centers hard against the Potomac River. Outdoor activities, like rafting, tubing, kayaking, golf, and hiking are all within walking distance. We are only short drive to Charles Town Casinos and Antietam Battlefield. We are fully licensed and support the community by paying occupancy tax.

Guest favorite

Farm stay in Harpers Ferry

5.0 out of 5 average rating, 225 reviews

The Lodge Room at Mt. Mama Meadows Homestead

This listing is adults only. Mt. Mama Meadows Homestead is our own slice of “almost Heaven”. We're located in Harpers Ferry, a small historic town in Jefferson County, West Virginia, in the lower Shenandoah Valley. Whether you are coming to check out the surrounding Blue Ridge Mountains, hike the Appalachian Trail, raft the Potomac or Shenandoah rivers, delve into the rich Civil War history of the area, or just relax on the homestead, there is no shortage of things to do.

Guest favorite

Apartment in Shepherdstown

4.91 out of 5 average rating, 140 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 favorite

Guest suite in Sharpsburg

4.93 out of 5 average rating, 179 reviews

Guest Apartment by C & O Canal and Battlefield

Affordable Luxury! 1200 square feet Bright & modern newly remodeled basement apartment with private entrance. Fully equipped kitchen, 2 BR, 1 BA. It’s on the ground floor of a newly renovated home. Hostess and boyfriend, Charles, live on top, main floor. Shepherdstown, WV 7 mi. C & O canal 1/3 mi. Antietam Battlefield 1/2 mi. Sharpsburg 2mi. Harpers Ferry 25 min. Hagerstown 10 min.Many cool breweries & wineries within 15 min. 7 mi to Rockland Estates venue.

Guest favorite

Apartment in Shepherdstown

4.98 out of 5 average rating, 119 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 favorite

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 510 reviews

Beautiful suite, spa bathroom & gardens

Private-entry luxurious suite combining comfort & style for a memorable stay. Located in quiet neighborhood -- Harpers Ferry historic district -- 1920s stone foursquare home with beautiful gardens to explore. Close to National Park, Potomac & Shenandoah Rivers, C&O Canal Trail, AT, Amtrak train station, Storer College, & Loudoun Co. wineries. An ideal accommodation for a romantic couple's getaway. More pics on Insta @rockhavenbnb