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, 577 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, 215 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

Guest suite in Sharpsburg

4.99 out of 5 average rating, 172 reviews

The River Bend Retreat ~ C&O Canal ~ Antietam

Welcome to The River Bend Retreat at Taylor's Landing: a relaxing get-away along the C&O Canal Towpath and the Potomac River. Whether you're in the area to enjoy the river and the towpath, soak up some history at Antietam National Battlefield, or explore the quaint nearby towns and attractions, we look forward to hosting your stay! The RBR's 2 bedrooms and 1 bathroom can accommodate up to 4 guests. Visit us online for even more details, information, and local recommendations. See you soon!

Guest favorite

Tiny home in Jefferson County

4.89 out of 5 average rating, 424 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.

Guest favorite

Treehouse in Shepherdstown

4.97 out of 5 average rating, 263 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

4.79 out of 5 average rating, 133 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

Rental unit in Shepherdstown

4.94 out of 5 average rating, 266 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.

Guest favorite

Home in Shepherdstown

4.95 out of 5 average rating, 221 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

Rental unit in Shepherdstown

4.91 out of 5 average rating, 149 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, 193 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

Rental unit in Shepherdstown

4.98 out of 5 average rating, 130 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

Rental unit in Shepherdstown

4.96 out of 5 average rating, 286 reviews

Downtown: Explore Shepherdstown from cozy 1br apartment

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.