Places to stay in Shepherdstown

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Top-rated places to stay in Shepherdstown

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Middletown

4.9 out of 5 average rating, 274 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Top guest favorite

A stone patio surrounded by Adirondack chairs encircles a fire pit, with flames dancing at the center. The cabin is set against a backdrop of lush green trees, and a hot tub is positioned nearby, offering a serene outdoor gathering space.

Chalet in Berkeley Springs

4.96 out of 5 average rating, 167 reviews

Exclusive Mountain Lodge and Unmatched Hospitality

Be Still, our flagship mountain retreat!Experience an elevated escape to Berkeley Springs 8 person Hot Tub 🌳Screened in porch+2 open Decks 🥾Direct access to hiking trails PRO TIP:leads to brewery 👙Community Pool+Kiddie Pool+Jacuzzi (seasonal) 🛋️3 Family Rooms 🪵Massive Firepit+provided Firewood+Grill 🔥Cozy Propane Fireplace 🎲Pool Table+Shuffleboard table+Board Games+DVD Library 📺WIFI+two 65in TVs 🛏️5 comfy bedrooms 💆🏼‍♀️5 FULL Bathrooms+1/2 bath 🛍️5 min to downtown Berkeley Springs

Guest favorite

The guesthouse exterior presents a gray facade with a welcoming porch. Lush greenery, including manicured bushes and large trees, frames the entrance. A paved walkway leads to the door, surrounded by planters. The house stands under a clear blue sky, providing a serene setting.

Guesthouse in Middletown

4.95 out of 5 average rating, 285 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Superhost

A warm-toned living area features a staircase leading to an upper level. The kitchen area is visible in the background, equipped with cabinets and appliances. A wooden dining table sits in the foreground, complemented by a cozy seating area with a patterned couch.

Loft in Winchester

4.72 out of 5 average rating, 648 reviews

Immerse yourself in Old Town Winchester (Apt #4)

Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops, and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky, and awesome, we are your place!

Guest favorite

The cabin is nestled among lush trees, showcasing a dark exterior with large windows and a spacious deck. A hot tub is located on a wooden platform, inviting relaxation amidst the serene woodland backdrop.

Cabin in Hedgesville

4.94 out of 5 average rating, 180 reviews

Hot Tub, Dog Friendly Boho Cabin in The Woods

Unwind at our secluded A-frame cabin in The Woods! Feel transported into the trees as you enjoy coffee on the screened-in porch, roast marshmallows by the fire pit, relax in the hot tub, or simply look out the expansive windows. Furry friends will feel at home with a built-in dog bowl station and two-acres for exploring. Just under two hours from the D.C./Baltimore area with a ChargePoint EV station in the driveway, it's the perfect all-seasons getaway for families and groups of friends.

Top guest favorite

Dome in Mercersburg

4.99 out of 5 average rating, 143 reviews

StayAround Dome ~ Unique & Tranquil Gem ~ Hot Tub

Welcome to the unique dome oasis, a one-of-a-kind experience in a secluded location just a few mins from Whitetail Resort. This architectural marvel boasts a luxury design, comforts, amenities, and spectacular views, providing a space for romantic getaways, creative inspiration, or a simple break from the ordinary. *Comfortable King BR *Open Design Living *Full Kitchen *Wraparound Deck (Hot Tub, BBQ, Fire Pit, Seating) *Smart TV *High-Speed Wi-Fi *Parking *EV Charger Learn more below

Guest favorite

A full bathroom is showcased with a modern vanity in a dark finish. A copper lounging tub and walk-in shower are present, along with a round mirror and neatly arranged towels. Light-colored shiplap walls and a window with privacy blinds enhance the space's brightness.

Townhouse in Harpers Ferry

4.88 out of 5 average rating, 51 reviews

1840 Home, Central Location in Harpers Ferry

Welcome to Rose Trellis - Avocet: Historic Comfort in Harpers Ferry! Experience this beautifully remodeled 1840 home at Rose Trellis - Avocet. Perfect for couples, this historic retreat features: Coffee station Functional kitchenette on the first floor Queen bedroom on the second floor Sitting room with a futon on the second floor Full bath with shower and copper lounging tub Off-street parking Gigabit Wi-Fi Old homes are drafty, it's best to bring a sweater.

Superhost

A welcoming front entrance features a wide staircase leading to a covered porch. The cabin's wooden exterior is complemented by multiple windows, allowing natural light to enter. Leafless trees stand tall in the background against a clear blue sky.

Cabin in Augusta

4.98 out of 5 average rating, 44 reviews

Enlightenment, Mountain View

A wonderful place to get away , solitude retreat to reflect! peaceful Enjoy peaceful surroundings, morning mist mountain view ,amazing sunset ,the campfire by yourself and watch the stars and the moon in the sky at night, the silence of the mountain, fresh air , green , pine tree ….. peaceful,private, quiet, country living, a great place for meditation. , a Japanese style (Tatami) for meditation/tea room . Green ,wood ,flowers ,color leaves , snow ……

Superhost

A spacious terrace deck is shown, featuring a seating area with a comfortable lounge sofa and a dining table for four. A grill is visible alongside a potted plant. Ambient lighting and a blue umbrella enhance the outdoor setting, with views of the surrounding greenery.

Apartment in Winchester

4.84 out of 5 average rating, 19 reviews

The Queen of Winchester - Three Bedroom Apartment

Nestled in the picturesque city of Winchester, the "Queen of Winchester" offers a tranquil escape in a prime location that perfectly blends convenience and comfort. This beautifully renovated three-bedroom apartment is situated on the upper level with a terrace deck, promising privacy and views of the surrounding area. Whether you're visiting for a relaxing retreat or a business trip, this property is designed to ensure a memorable and luxurious stay.

Top guest favorite

A serene garden space is surrounded by lush greenery and tall trees. Relaxing lounge chairs are positioned on a gravel path, which is bordered by decorative stones. Soft lighting strung among the trees adds a tranquil ambiance to the outdoor setting.

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 585 reviews

Beautiful suite, spa bathroom & gardens

Private-entry luxurious suite combining comfort & style for a memorable stay. Located in quiet neighborhood -- Harpers Ferry historic district -- 1920s stone foursquare home with beautiful gardens to explore. Close to National Park, Potomac & Shenandoah Rivers, C&O Canal Trail, AT, Amtrak train station, Storer College, & Loudoun Co. wineries. An ideal accommodation for a romantic couple's getaway. More pics on Insta @rockhavenbnb

Top guest favorite

A serene creek runs through a wooded area, surrounded by lush greenery and vibrant autumn leaves. A rustic structure featuring an outdoor kitchen and dining space is visible beside the creek, complemented by soft lighting strung overhead.

Campsite in Front Royal

4.98 out of 5 average rating, 181 reviews

Blue Mountain Hideaway- Unique Glamping Experience

Escape to our serene creek-side glamping retreat, where nature meets comfort. This private paradise offers hassle-free camping—just bring your cooler and clothes, we provide the rest! Relax by the creek, explore Shenandoah National Park, and enjoy cozy evenings around the campfire. With a comfortable bed, a fully equipped outdoor kitchen, and complementary firewood, your perfect escape awaits. Book your stay today!

Top guest favorite

A charming multi-story home features a light-colored wooden exterior, complemented by stone pathways and a staircase. Flags adorn the exterior, and a spacious deck area is visible, surrounded by greenery. The building's architectural details showcase a blend of historical and modern design.

Home in Harpers Ferry

4.94 out of 5 average rating, 395 reviews

Gayte House Gay Owned, Liberal Oasis

Cozy and charming 1840's home in the heart of town. Steps from the National Park, feet from the Appalachian Trail. Relax by the fire, on the porch or on the river. We have something for every season and every age. Steve and I have lived here In HF 20 yrs., 13 of those at the Gaytehouse. We live right next door now and Love both our homes. Please, Check out the beautiful and cherished home we offer for your stay.