Vacation rentals in Sharpsburg

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.

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.

C&O Canal/Potomac River Lock Keepers 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.

Guest Apartment by C & O Canal and Battlefield

Luxurious, modern comfort with KING & QUEEN sized super comfy beds.Newly remodeled. 3min to center of Sharpsburg in quiet country setting, w/1200 square ft. of space that’s all one level inside. Bright & modern basement apartment with private entrance. Firepit and beautiful outdoor seating. Lots of large windows and natural light. Fully equipped kitchen, 2 BR, 1 BA. It’s on the ground floor and Hosts live on top, main floor. Shepherdstown 7 mi. C & O canal 1/3 mi. Antietam Battlefield 1/2mi

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.

❤️ 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 3 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.

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

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

Oak Hill Private Suite Historic North End

A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

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.

Steps to Winery and Battlefield | 1-Acre Retreat

Unwind at this breathtaking 1-acre hilltop retreat overlooking Antietam Battlefield and lush vineyards. Perfect for a romantic escape or family getaway, our newly remodeled home offers stunning views from the deck, cozy interiors, and easy access to Antietam Creek Vineyards—just a short walk away. Explore nearby trails, relax by the outdoor fire pit under the stars, and enjoy the peaceful setting while experiencing all the comforts of home.

Downtown: Explore Shepherdstown from cozy 1br apar

Welcome to our cozy and modern one-bedroom apartment, located just steps away from history, dining options, the beautiful outdoors, and Shepherd University campus! You'll enjoy the convenience of being right on the street while still having a peaceful and private escape from the downtown hustle and bustle. Nestled in downtown Shepherdstown, easily explore downtown, while also being a short walk away from the Potomac River.