Vacation rentals in Shepherdstown

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Top-rated vacation rentals in Shepherdstown

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Top guest favorite

A spacious sleeping area is centered around a beautifully made bed with a textured gray coverlet. Nightstands on either side feature stylish lamps and small potted plants. Art is displayed on the wall, contributing to a serene atmosphere, with natural light filtering through the window.

Guest suite in Shepherdstown

4.96 out of 5 average rating, 688 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 cozy front porch is framed by brick columns and adorned with vibrant plants in terracotta pots. Steps lead up to the porch, where a small table and chairs are visible, inviting relaxation amidst the lush greenery of the surrounding garden.

Guest suite in Shepherdstown

4.99 out of 5 average rating, 250 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

A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.

Tiny home in Harpers Ferry

4.97 out of 5 average rating, 143 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Top guest favorite

A modern studio with open wooden beams features a cozy seating area and a spacious bed adorned with a textured blanket. Natural light filters through large windows, illuminating the space. A round table and a small stool complement the inviting layout, with deck access visible.

Tiny home in Shepherdstown

4.99 out of 5 average rating, 165 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.

Superhost

A welcoming living area features a comfortable gray sofa with colorful cushions, accompanied by a plush armchair. Natural light filters through large windows, offering views of the river. A decorative rug adds warmth, while a coffee table and a cozy chair complete the space.

Cottage in Shepherdstown

4.91 out of 5 average rating, 285 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 charming log cabin features a spacious front porch with rocking chairs, surrounded by trees and blooming flowers. The roof shows aged metal, and windows are adorned with shutters, inviting natural light into the home. A landscaped garden area is visible in the foreground.

Home in Sharpsburg

4.98 out of 5 average rating, 146 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 among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.

Treehouse in Shepherdstown

4.97 out of 5 average rating, 362 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.

Top guest favorite

The exterior of a two-story cottage is presented, featuring a blend of dark green siding and stone accents. Large windows are illuminated, highlighting a welcoming entrance. Surrounding trees are bare, indicating the season, while a spacious yard of grass and earth is visible in the foreground.

Cottage in Shepherdstown

4.97 out of 5 average rating, 169 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

Top guest favorite

A charming view of downtown Shepherdstown showcases a row of historic buildings, each displaying unique architectural features. A vibrant green tree adds a touch of nature, while a clear blue sky enhances the picturesque streetscape.

Apartment in Shepherdstown

4.97 out of 5 average rating, 208 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

A charming outdoor seating area is framed by a stone wall, featuring two orange chairs and a small table. The entrance is marked by a bright red door, flanked by lantern-style wall lights and surrounded by small shrubs and landscaping.

Home in Shepherdstown

4.95 out of 5 average rating, 260 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.

Top guest favorite

A charming two-story cottage features a welcoming front door framed by decorative shutters and flower planters. A covered porch is seen to the left, adding outdoor space for relaxation. The surrounding yard is well-maintained, providing a pleasant view of the greenery.

Cottage in Shepherdstown

5 out of 5 average rating, 120 reviews

The Creekside Cottage: Downtown | Pet-Friendly

Welcome to the Creekside Cottage, a 2 bedroom/1.5 bathroom spacious home, offering a secluded escape by the creek yet just a short stroll through the gardens of Shepherdstown to shopping and dining. Perfect for getaways, family visits, or university stays, this Creekside Cottage offers a roomy interior, cozy living room, modern kitchen, fire pit, and a private patio & porch to be enjoyed along the Town Run.

Top guest favorite

A restored log cabin features a red metal roof and wooden exterior, framed by trees and a grassy area. A dog lies comfortably on the ground in front of the porch, which is adorned with red chairs and a lantern.

Cabin in Shepherdstown

4.95 out of 5 average rating, 492 reviews

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.