Places to stay in Shepherdstown

4.9 out of 5 average rating, 273 reviews

Cottage in Middletown

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

JesseRating, 5 stars6 days ago

Heather was amazing. Very responsive and answer all questions I had right away. Her home was amazing it was like home away from home. I would recommend heather anytime. Best air bnb host yet. I would highly recommend people to check this property out you will fall in love. Thanks heather for everything. Your home was very clean and welcoming.

4.94 out of 5 average rating, 179 reviews

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

Hot Tub, Dog Friendly Boho Cabin in The Woods

BenjaminRating, 5 stars1 week ago

I keep coming back to this place and increasingly consider it a home away from home. It is inviting and cozy and at the same time full of fun stuff like games, stocked full of kitchen and bar implements, fireplace -- perfect for large groups of friends, though I usually go with my wife and daughter as an escape for work. It is a short drive to places like Harper's Ferry, where we went this time to hike part of a Appalachian Trail. Alexa and Andy were responsive, and prompt and friendly, in their responses, as usual. We will most certainly be going back within the next year.

Chalet in Berkeley Springs

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.

4.96 out of 5 average rating, 165 reviews

Exclusive Mountain Lodge and Unmatched Hospitality

AlliRating, 5 stars2 weeks ago

We planned a special weekend getaway to celebrate my sister’s upcoming July wedding, and this place was absolutely perfect for it! Our other sister and I organized a cozy, fun-filled weekend for her and her closest friends, and it couldn’t have gone better. The home was clean, well-organized, and easy to navigate—everything worked seamlessly. The fireplace and hot tub were definitely highlights and made the whole experience even more memorable. We truly have no complaints and will cherish the memories we made here forever. Highly recommend!

4.95 out of 5 average rating, 283 reviews

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

Indulge, Fresh Flowers, Frederick County Haven

SamuelRating, 5 stars3 days ago

This excellent little guest house was great for me and my friends. When we were making a trip up to Connecticut as a halfway stop. Everything was clean and simple and the host was excellent and getting us checked in easy because we had been on a long road trip. Couldn't have asked for an easier place to stay.

4.72 out of 5 average rating, 647 reviews

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

Immerse yourself in Old Town Winchester (Apt #4)

JimRating, 5 stars3 days ago

I had a great one-night stay! I had a free evening before a work meeting and this spot made it so easy to explore downtown Winchester. It's a stone's throw away from the library (must see for architecture enthusiasts), and literally around the corner from the north end of the Walking Mall. The space was cozy and stocked with the essentials. The bed was super comfortable and the quiet made it easy to sleep. I highly recommend Maureen's place!

Townhouse in Harpers Ferry

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.

4.88 out of 5 average rating, 50 reviews

1840 Home, Central Location in Harpers Ferry

DanRating, 5 stars2 weeks ago

Very clean, comfortable and tastefully decorated cottage. It had everything we needed to make our first trip to Harpers Ferry memorable. It is a great location for sightseeing and exploring Harpers Ferry and surrounding historic sites.

4.94 out of 5 average rating, 124 reviews

A spacious backyard features lush green grass and a patio area with seating, alongside a firepit. A deck with a large umbrella is visible, providing an inviting space for relaxation. The surrounding scenery includes trees and distant fences, creating a peaceful outdoor setting.

Guest suite in Leesburg

Stunning Views in Spacious Unit

LoriRating, 5 stars1 month ago

We loved our stay. It was spotless, safe, and so comfortable. It was just beautiful. I enjoyed sitting on the patio at night with my kindle and a glass of wine. It is also super convenient to our children and grandchildren. We definitely plan to stay here in the future.

4.98 out of 5 average rating, 44 reviews

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

Enlightenment, Mountain View

JasonRating, 5 stars6 months ago

Another peaceful stay for a solo meditation retreat! Su, Sy, and Philip are always responsive and make sure visitors have a great stay. The cabin was very clean and spacious, and I enjoyed spending time on the front porch watching all the local wildlife. I'll be back again!

4.84 out of 5 average rating, 19 reviews

The exterior of a charming two-story building is shown, featuring a soft gray color. A covered porch is seen, with columns supporting the roof. Lush greenery surrounds the property, and a paved entrance leads to the main door, creating a welcoming access point.

Apartment in Winchester

The Queen of Winchester - Three Bedroom Apartment

LeonRating, 5 starstoday

Everything was great the 3rd room is s loft. It was everything that we needed when we stayed working on a project at Shenandoah University. Everything is a five to ten minute drive. Space was clean and cozy. The back deck was a cool chill out area.

Guest suite in Harpers Ferry

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.

4.98 out of 5 average rating, 584 reviews

Beautiful suite, spa bathroom & gardens

ManuelaRating, 5 stars1 day ago

My first Airbnb experience and roadtrip was amazing. I didn’t want to leave, it was so beautiful, peaceful, and comfortable. Thank you Lynn and Christian for sharing your beautiful home with me and fellow travelers and making it feel like a home away from home. I hope to be back very soon. 🙂

4.98 out of 5 average rating, 178 reviews

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

Blue Mountain Hideaway- Unique Glamping Experience

SarahRating, 5 stars2 weeks ago

We had a fantastic stay at this hideaway! Despite a rainy trip, it was still such a peaceful weekend. We are already thinking about when our next trip will be! Highly recommend this little slice of heaven 🤍

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Popular amenities for Shepherdstown places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Shepherdstown's top sights

Bavarian Inn, Resort and Brewing Company47 locals recommend

Blue Moon Cafe47 locals recommend

Press Room43 locals recommend

Maria's Taqueria23 locals recommend

The Mecklenburg Inn23 locals recommend

Opera House19 locals recommend

Other great vacation rentals in Shepherdstown

4.93 out of 5 average rating, 114 reviews

Home in Sabillasville

Stoney Spring Overlook

DanielleRating, 5 stars3 weeks ago

We stayed at this property the weekend of our wedding and it was perfect! The house and surrounding area were absolutely BEAUTIFUL!!! It was clean and stocked well with supplies. All the amenities listed were present and functioned well. Jeanne was a wonderful host! She was very responsive and made us feel right at home! We couldn't recommend this Airbnb more and can’t wait to visit again!

4.87 out of 5 average rating, 124 reviews

An open living space features wood-tone floors and high ceilings, illuminated by natural light. A vintage kitchen island provides a gathering spot, while a cozy seating area includes a sofa and armchair. Large windows offer views of the surrounding countryside.

Home in Cross Junction

The Little Red Schoolhouse

JackelynRating, 5 stars1 week ago

Beautiful views and very peaceful to get away!

4.83 out of 5 average rating, 248 reviews

Home in Harpers Ferry

Larger Families, Hot tub, Campfire Ring, Rural

AdrienRating, 5 stars4 weeks ago

Home was clean and as described. It was large and roomy. Outside had a nice yard to play in. Harper’s Ferry town and the national historic park are amazing places to visit. Lots to do and see even in March. I would visit again and stay at this home again.

4.9 out of 5 average rating, 201 reviews

A soft morning light fills the landscape, highlighting a winding river framed by lush green forests and rolling hills. Mist lingers above the water, creating a serene and tranquil atmosphere as the sun rises over the horizon.

Cabin in Great Cacapon

Cabin Getaway: Hot Tub ☆ Privacy ☆ Views

BethanyRating, 5 stars4 weeks ago

Great stay! Comfortable, clean and great location. Daniel was very informative and responded quickly. Would definitely stay again!

4.81 out of 5 average rating, 436 reviews

The cabin's living area features a warm wood interior with vaulted ceilings and large windows offering views of the lake. A comfortable brown leather sofa is positioned near a coffee table, complemented by two wooden armchairs. A cozy wood stove adds to the inviting atmosphere.

Cabin in Harpers Ferry

Cozy Cabin Hidden Away on a Lake!

PaulaRating, 5 stars1 week ago

The place was exactly as pictured. Very cozy and loved having water views everywhere. Definitely recommend it!

4.94 out of 5 average rating, 140 reviews

An aerial view of the great room reveals a cozy seating area with an orange sectional sofa and a coffee table, situated around a gas fireplace. High ceilings and large windows fill the space with natural light, and a dining table for six complements the open layout.

Cabin in Hedgesville

Starcatcher Chalet, The Woods Resort

MargaritaRating, 5 stars1 week ago

A very welcoming place and has many forms of entertainment for both adults and children.

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 109 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Marissa MarieRating, 5 stars2 weeks ago

we stayed at Alisons place for a girl's weekend. It was beautiful! the pictures are exactly how the place looks, decorated nicely and very very clean. the host communicated very well and quickly, even had alot of recommendations for food and things to do. highly recommend staying here!