Holiday rentals in Shepherdstown

Guest suite in Shepherdstown

4.96 out of 5 average rating, 661 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 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!

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.

4.9 out of 5 average rating, 271 reviews

Cottage in Shepherdstown

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 suite in Sharpsburg

4.94 out of 5 average rating, 250 reviews

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 1/2 mi

Guest favourite

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.

Treehouse in Shepherdstown

4.97 out of 5 average rating, 340 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 favourite

Flat 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.

Guest favourite

Flat in Shepherdstown

4.92 out of 5 average rating, 197 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.

4.97 out of 5 average rating, 190 reviews

Flat in Shepherdstown

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!

4.95 out of 5 average rating, 254 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.

4.96 out of 5 average rating, 156 reviews

Home in Sharpsburg

Steps to Winery & Battlefield-Pvt Acre w/ Hot Tub!

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, a relaxing year-round hot tub, cozy interiors, and easy access to Antietam Creek Vineyards—just a short walk away! Explore nearby trails or soak under the stars in the hot tub, all while enjoying the comforts of home.

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Other great holiday rentals in Shepherdstown

4.73 out of 5 average rating, 26 reviews

Shepherdstown Farmhouse Retreat - 3br/2bath

GerilynRating, 5 stars1 month ago

Perfect location if you’re interested in strolling around town, looking walking through the shops and exploring local dining. So glad we chose the location! Perfect for graduation weekend, when everything was happening at once, it was easy for anyone to do what they needed or wanted to do on foot. The place is very clean and the beds are super comfortable. Easy to get in and easy to get out! Would totally recommend and would definitely go back!

4.97 out of 5 average rating, 65 reviews

Welcome to our cute and cozy rocky garden cabin.

SueRating, 5 stars1 week ago

Lovely accommodations. Everything was spotless and well appointed. Everything you could need for kitchen supplies. Very comfortable bed. Linens and towels were soft. Because it is a 1800’s home, the floors are uneven and the steps are steep and narrow. So be careful if you have balance or mobility issues. Hosts were very responsive. Recommend to everyone.

Campervan/Motorhome in Hedgesville

5 out of 5 average rating, 24 reviews

Explore Creekside RV Bliss

SamRating, 5 stars1 week ago

Such a nice place right by the water. Comfy bed and fun to cook on the fire! Highly recommend!

5 out of 5 average rating, 3 reviews

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

JamieRating, 5 stars5 days ago

We had a wonderful weekend in this sweet cabin! From before check in, until check out Flora made the whole experience easy and comfortable. There are so many thoughtful details throughout this property. Super clean and beautiful inside, but we spent most of our time enjoying the incredible deck. Our favorite part was that we could still sit outside in comfy seats and watch a thunderstorm while covered! Close to lots, but far from it all. We can’t wait to come back!

4.98 out of 5 average rating, 41 reviews

Cottage in Harpers Ferry

Firehouse Cottage | Walk to all of downtown HF

JulieRating, 5 stars1 day ago

Firehouse Cottage was just perfect for our overnight stay in Harper's Ferry. The size was just right for 2 people and I was amazed how many amenities fit into the place (and how well they fit, too). The cottage is small but somehow also spacious - efficient is what I'd call it! The location is ideal and just a short walk to Lower Town restaurants and the NPS site. We drove to Shepherdstown for dinner and that was an easy drive from the cottage. Great location, clean and tidy, free parking, and plenty of amenities make this a great place for 1-2 people.

4.86 out of 5 average rating, 28 reviews

Welcome to the Shepherds Rest

DanielRating, 5 stars3 weeks ago

This place was perfect weekend getaway for my young family on our bike trip. There was also a shed to store bikes which was great. Wonderful convenient location, with walking distance to the main street and delicious restaurants. John was kind and quick in his responses. I would highly recommend and definitely come back.