Places to stay in Shepherdstown

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Top-rated places to stay in Shepherdstown

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Top guest favorite

A well-lit bathroom area is visible, featuring a modern toilet and a decorative rug with a circular pattern. Natural light enters through a window adorned with blinds, while a framed artwork adds a touch of character to the space.

Guest suite in Shepherdstown

4.96 out of 5 average rating, 660 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.

Top guest favorite

A black electric vehicle is parked beside a brick home, connected to a charging station. Surrounding foliage displays autumn leaves. The paved pathway leads to the entrance of the house, contributing to the overall garden ambiance.

Guest suite in Shepherdstown

4.99 out of 5 average rating, 239 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!

Top guest favorite

Tiny home in Shepherdstown

4.99 out of 5 average rating, 146 reviews

Studio: Downtown Hideaway & Waterside Garden Oasis

Our modern studio is on the Town Run and steps away from downtown Shepherdstown. Whether you’re here for a relaxing escape or a university visit, listen to a waterfall from our cozy, zen, spa-like space with outdoor gardens. It’s an oasis with a comfortable full bed, dedicated work area, and walk-in shower. Nestled in historic downtown, you can easily explore German St., with a variety of dining options, shopping, and outdoor activities a short walk away from the Potomac River and C&O tow path.

Top guest favorite

Cottage in Sharpsburg

4.96 out of 5 average rating, 180 reviews

C&O Canal/Potomac River cottage

Located just steps away from Dam #4 on the C&O Canal / Potomac River. (marker 84.6) Perfect for a getaway or romantic weekend. Hike/bike the C&O Canal, bring your kayak/canoe/bikes, fish or swim in the river. Sit on the porch and listen to the rumble of the water falling over the dam. Local lore is this was the home of a canal lock keeper or the gate house keeper. Secluded location away from town. NOT A PARTY HOUSE/owner on site in garage apartment. Inquire if a blocked day is available.

Superhost

The tranquil river is illuminated by the soft glow of moonlight reflecting off the water's surface. Silhouetted trees frame the scene against the night sky, which is dotted with clouds and stars. Fallen leaves create a natural foreground.

Cottage in Shepherdstown

4.9 out of 5 average rating, 271 reviews

Riverfront Cottage in Shepherdstown, WV

Escape to this tranquil, riverfront retreat with stunning, year-round river views, a private dock (available late May-Sept) & firepit. Relax, fish, explore, or visit nearby attractions in Shepherdstown, Sharpsburg, & Harper's Ferry. Two kayaks, a canoe, paddles, & lifejackets are available for your use. All water activities are at your own risk. WV DNR requires all boaters to have a lifejacket and all boats to have a whistle. Please bring your own whistle(s). MD or WV fishing license is fine.

Guest favorite

A calm river stretches ahead, flanked by lush greenery on both banks. The stillness of the water reflects the surrounding trees, creating a tranquil scene. A paddle is held in the foreground, indicating an active exploration of the serene environment.

Tiny home in Jefferson County

4.89 out of 5 average rating, 475 reviews

❤️ Secluded 1940s Romantic Tiny House on the River

Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 2.5 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

Top guest favorite

Home in Sharpsburg

4.99 out of 5 average rating, 137 reviews

Charming Historic Canal House C&O Potomac Antietam

The Canal House at Taylors Landing. We are in the countryside, bordering the Chesapeake & Ohio Canal Historic National Park, 2 miles from the Civil War's Antietam Battlefield. Our home is an original 1790 log cabin with 1857 additions, also features modern amenities, including a chef's kitchen. Multiple outdoor venues, extensive grounds and amazing views of a 4-seasons garden, the C&O Canal National Park, and the Potomac river. Enjoy a creative retreat, nature, history, adventure, romance.

Top guest favorite

The treehouse is perched 20 feet above a rocky outcropping, supported by large oak and hickory trees. Bright green leaves offer a natural canopy, framing the structure which features several windows, inviting natural light into the space.

Treehouse in Shepherdstown

4.97 out of 5 average rating, 339 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.

Guest favorite

A modern kitchen is showcased with sleek gray cabinetry and stainless steel appliances. A lighting fixture adds warmth, while a book rests open on a glass table in the foreground. High-top bar stools are positioned nearby, creating an inviting space.

Apartment in Shepherdstown

4.95 out of 5 average rating, 141 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 modern kitchen corner is highlighted by a granite countertop and a deep sink. Overhead, natural light filters through two windows, while appliances, including a microwave and coffee maker, are neatly arranged. Decorative baskets are positioned underneath the counter for extra storage.

Apartment in Shepherdstown

4.94 out of 5 average rating, 330 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

Top guest favorite

The historic downtown apartment building features a classic architectural style with a white brick facade. Large windows allow natural light to fill the space, while a welcoming red front door adds a pop of color. A tree provides shade in front, enhancing the street view.

Apartment in Shepherdstown

4.97 out of 5 average rating, 189 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!

Top guest favorite

Home in Shepherdstown

4.95 out of 5 average rating, 253 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.