Shepherdstown Vacation Rentals

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Vacation Rentals in Shepherdstown

Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 9 - Jun 10
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, (18)
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is $94
$216 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Cottage
Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, (20)
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
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Fridge, microwave, oven, stovetop
Welcome to this patch of serenity on the river's edge, to this hideaway.
9.8 out of 10, Exceptional, (57)
"We had a really lovely time at this space, Amy was such a good host, and we hope to return!"
Welcome to this patch of serenity on the river's edge, to this hideaway.
Property grounds
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, (51)
"Beautiful historic toll house. very comfortable and well stocked ..you wont be disappointed"
Antietam Toll House~ an historic waterfront cabin
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (28)
"This little cabin was great!! Comfortable beds. Very clean. Brigid the host was so responsive. Instructions were very clear. She even answered our questions about recommendations for a goos hiking trail! Highly recommend! I hope we will be back."
The price is $145
$328 total
includes taxes & fees
May 29 - May 30
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (50)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.6 out of 10, Exceptional, (8)
"Beautiful property, quiet, and very spacious. This property had everything we were looking for in a getaway. My family enjoyed our time together here. We did have a power outage and I let Tony know as soon as the power went out. He was quick to respond and even gave updates. Loved the communication from Tony throughout our whole experience. Definitely would stay here again and at another one of his properties."
The price is $115
$287 total
includes taxes & fees
May 29 - May 30
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (61)
"Beautiful views from the wrap around porch. Comfortable inside including the bed. Lots of neat things to look at. Highly recommend!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Fridge, microwave, oven, stovetop
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
9.8 out of 10, Exceptional, (32)
"A diamond in such a remote area, the host has really gone above and beyond to make a relaxing and accommodating stay."
The price is $170
$317 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (100)
"Perfect location in historic Middletown. Our daughter stayed over night to be our driver to graduations. She recommends a circulating fan for the basement bedroom! Apparently, we, at the age of 83, kept the house a little too warm!"
The price is $145
$307 total
includes taxes & fees
Jun 2 - Jun 3
Charming "Cream of the Crop" Cape ~❤️of Middletown
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is $145
$221 total
includes taxes & fees
Jun 2 - Jun 3
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (8)
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Interior
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, (17)
"We had previously visited Frederick last November and had only been able to spend a little bit of our visit in Historic Frederick. We loved staying in historic Frederick and the property was unique, very clean and well laid out. I should have realized was that 'penthouse' in a historic home would mean steps. I am blind in one eye and have poor physical balance so carrying luggage up stairs is challenging. Nonetheless, we loved the layout and amenities of the property. The view from the deck was...
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Interior detail
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
9.8 out of 10, Exceptional, (207)
"Had a great time at this property and were able to take advantage of the screened in porch and fireplace. Neighborhood was very nice and checkin was easy. They were very accommodating for the three dogs that also visited the property with us."
Beautiful Cottage At 'the Woods' Resort, Golf, Spa, Swimming & Resort Amenities
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (93)
"We had a lovely stay in this beautiful Harpers Ferry home. It was so amazing to stay in the historical area and be close and able to walk to all the National Park sites. We were most attracted to that lovely porch and enjoyed our coffee there in the early morning, watching the town come to life. We also liked afternoons reading and napping there and an evening glass of wine after dinner. The kitchen was well stocked with everything we needed, the furniture and beds were very comfortable. We will...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Property grounds
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, (9)
"The location tucked away on the lake with a dock and kayaks and gravity lounge chairs, fireplace, large dock and gas grill were fabulous."
Rustic Log Cabin with Private Dock on the Lake!
Property grounds
The Oculus - Huge Cabin with a Hot Tub!
10.0 out of 10, Exceptional, (11)
"This property is so wonderful. Great location. Wonderfully comfortable beds! And very clean! We look forward to coming back!"
The Oculus - Huge Cabin with a Hot Tub!
View from property
Antietam Creek - Quiet 2 Bedroom Cabin
9.4 out of 10, Exceptional, (71)
"Perfect quiet spot to relax and spend quality time! Cabin was as listed and was just what we needed!"
The price is $200
$332 total
includes taxes & fees
May 28 - May 29
Antietam Creek - Quiet 2 Bedroom Cabin
Don't see what you're looking for?
See all available properties in Shepherdstown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Shepherdstown you may be interested in

Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 9 - Jun 10
❤️ Secluded 1940s Romantic Tiny House on the River
Room, 2 Queen Beds, Non Smoking | Premium bedding, down comforters, pillowtop beds, in-room safe
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1010)
"Very nice and affordable place, exceeded my expectations because the price, i read the reviews before reservation and were good and that gave me more confidence, very convenient to my needs, now if you are a person that uses a magnifier to find any problems you’ll find it, I was happy with my staying and willing to it again."
The price is $81
$90 total
includes taxes & fees
Jun 16 - Jun 17
Country Inn & Suites by Radisson, Frederick, MD
Exterior
Hilton Garden Inn Frederick
3.0 star property
9.0 out of 10, Wonderful, (1007)
"Room was clean and hotel staff very nice "
The price is $112
$124 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Garden Inn Frederick
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Shepherdstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherdstown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shepherdstown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherdstown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shepherdstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shepherdstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherdstown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherdstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental in Shepherdstown?

Welcome to this patch of serenity on the river's edge, to this hideaway.: Visitors give good reviews to this Shepherdstown vacation home rental, which is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Shepherdstown?

Expedia has 9 vacation rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Rumsey Steamboat Museum are other places worth a visit.

What’s a vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.

Recent reviews of Shepherdstown properties
Expedia verified reviews

Apm Inn & Suites

Apm Inn & Suites

4/5 Good
"Good spot. Good price. "
A verified traveler stayed at Apm Inn & Suites
Posted 11 hours ago
Apm Inn & Suites