Places to stay in Shepherdstown

Guest suite in Shepherdstown

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.

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

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.

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.

4.96 out of 5 average rating, 180 reviews

Cottage in Sharpsburg

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.

Tiny home in Jefferson County

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.

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

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.

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.

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.

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.

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.

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

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.

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!

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.

A modern kitchen countertop is equipped with a Keurig coffee maker, accompanied by a carousel of coffee pods. A bag of popcorn sits nearby alongside a small kettle and cooking utensils in a ceramic container. Simple décor enhances the functional space.

4.95 out of 5 average rating, 350 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.

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Popular amenities for Shepherdstown places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Shepherdstown

A colonial farmhouse with a welcoming front porch is surrounded by lush greenery. Large windows allow natural light to illuminate the exterior walls. The sloped yard features a mix of trees and open space, contributing to a serene outdoor environment.

4.72 out of 5 average rating, 25 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!

A rustic barn, showing weathered wooden siding, is partially shaded by lush green trees. Surrounding vegetation includes a variety of plants and shrubs, contributing to a serene, natural setting. The grass is well-maintained, leading towards the barn's entrance, which features a covered area.

4.97 out of 5 average rating, 64 reviews

Welcome to our cute and cozy rocky garden cabin.

LizaRating, 5 stars2 months ago

Stacey’s apartment was clean and thoughtfully arranged to provide so many extra kitchen and bathroom items. It was kind and definitely over-the-top!!!! She also generously offered to help with some car trouble I was having. I would stay there again for sure.

5 out of 5 average rating, 57 reviews

Exclusive Wooded Chalet w/ Magnificent River Views

HeatherRating, 5 stars2 weeks ago

We chose this house for the view and it did not disappoint. Beautiful. House is exceptionally clean and very modern. Bedding is so soft!! Highly recommend this house and we would def stay here again!!!

Cabin in Sharpsburg

5 out of 5 average rating, 3 reviews

Antietam Retreat at Blue Haven

KarenRating, 5 stars3 days ago

Lovely location, down a semi-private drive, surrounded by nature, and with a very responsive host. A few things for the prospective AirBnber to note: 1) Only a mini-fridge is available for you. The host keeps the main fridge for personal use. I didn't realize this until kind of late in the game. 2) Parking is not far but also maybe 25 yards? away. If you have a lot of stuff (hopefully not food you are trying to put in the mini-fridge) or are not able-bodied, it could be a bit difficult. 3) There is just a railing that separates the second floor drop from the first floor. If you have small kids of poor judgment, I would not recommend letting them up there! 4) Not recommended to drink the tap water, also disclosed a little late. 5) There is a pump or fan or some kind of mechanized noise running constantly from the porch which makes it a little hard to focus on the quiet sounds of the koi pond. If there is a way to turn this off or down it wasn't obvious!

5 out of 5 average rating, 24 reviews

A metal sign reading 'BEACH ACCESS' is positioned on a grassy area near a tree. The background features trees and a serene natural setting, indicating a pathway to nearby beach access.

Camper/RV in Hedgesville

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!

4.88 out of 5 average rating, 8 reviews

A modern kitchen setup is displayed, featuring a sleek coffee maker on a polished granite countertop beside a shiny kettle. The stove is visible below, showcasing dual knobs for temperature control. A door handle can be seen, adding to the inviting kitchen atmosphere.

Home in Sharpsburg

Elevated Potomac River Retreat

AmandaRating, 5 stars1 month ago

Beautiful spot if you’re looking to be in the middle of nowhere and the middle of everything at the same time! Spent time exploring Shepherdstown, Sharpsburg, Boonsboro and Harper’s Ferry (all within 30 mins!) yet still felt secluded on this little home off the beaten path. Beautiful home, great host. Would recommend

Superhost

A wooden deck is seen featuring two outdoor chairs, inviting relaxation. The space is flanked by sliding doors, allowing for natural light to filter in. Lush greenery is visible in the background, offering a serene environment.