Shepherdstown Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Shepherdstown vacation rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (73 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
$120 nightly
The price is $133
May 4 - May 5
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (18 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
$433 nightly
The price is $470
Apr 27 - Apr 28
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$309 nightly
The price is $328
Apr 26 - Apr 27
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Property grounds

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (44 reviews)
"Loved the place and area."
United States
Steve R.
$301 nightly
The price is $335
May 5 - May 6
Total with taxes and fees
Charming Cabin in the Woods with River Access
Apartment (3 Bedrooms) | Front of property

2 Mi to Dtwn Frederick: Updated Townhome

2 Mi to Dtwn Frederick: Updated Townhome
4.0 star property
Frederick
$468 nightly
The price is $496
Apr 26 - Apr 27
Total with taxes and fees
2 Mi to Dtwn Frederick: Updated Townhome
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (199 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
$165 nightly
The price is $175
Apr 26 - Apr 27
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
$344 nightly
The price is $392
Apr 26 - Apr 27
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Dining

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (87 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$297 nightly
The price is $331
Apr 26 - Apr 27
Total with taxes and fees
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Property grounds

Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Absolutely amazing stay. Tom and Karen are amazing hosts. Cabins and property were spotless. Plenty of seating. Quiet and private and cant wait to go back again. Already planning next years weekend. Thank you for opening up your property to us all and treating us so well. "
United States
Christopher J.
$343 nightly
The price is $382
Apr 26 - Apr 27
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
Casino

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (45 reviews)
"We only stayed 2 nights for a little getaway, but this fit the bill perfectly. Everything was clean and comfortable, and the host was very responsive. Will be looking to stay again when the weather is warmer! "
United States
Matthew M.
$282 nightly
The price is $314
Apr 26 - Apr 27
Total with taxes and fees
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (86 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
$271 nightly
The price is $287
Apr 28 - Apr 29
Total with taxes and fees
Luxury Condo In Downtown Frederick
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.4 out of 10, Very Good, (5 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
$252 nightly
The price is $261
Apr 29 - Apr 30
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
Terrace/patio

Hillside Hideaway in Lowertown Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (20 reviews)
"The house is in a perfect spot to explore downtown Harpers Ferry! So much history within walking distance and so many beautiful homes. "
United States
Anonymous traveler
Hillside Hideaway in Lowertown Harpers Ferry
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
$222 nightly
The price is $235
Apr 29 - Apr 30
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
$175 nightly
The price is $186
Apr 27 - Apr 28
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Property grounds

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (100 reviews)
"Beautiful location! The host was extremely responsive with any questions most texts were returned within minutes! Will definitely stay here again. "
United States
Michael R.
$214 nightly
The price is $237
Apr 27 - Apr 28
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
1 bedroom, premium bedding, down comforters, laptop workspace

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
9.8 out of 10, Exceptional, (9 reviews)
"Clean room, spacious intimate setting "
United States
Camille
$403 nightly
The price is $431
Apr 26 - Apr 27
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Interior

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
$145 nightly
The price is $161
Apr 26 - Apr 27
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
Property grounds

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"Perfect place to spend a few nights with our two dogs. Very clean, great amenities, and beautifully decorated. Highly recommend!! "
United States
Megan L.
$410 nightly
The price is $446
Apr 26 - Apr 27
Total with taxes and fees
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
TV, foosball, books

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
$160 nightly
The price is $170
May 4 - May 5
Total with taxes and fees
Cozy Pine Tree Nest
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherdstown Hotel Reviews

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Staff friendly!"
peter 1-night trip
Posted 20 hours ago
Hampton Inn Martinsburg

Find out more about Shepherdstown

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 $133 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.

Explore a world of travel with Expedia

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?

Exclusive Wooded Chalet w Magnificent River Views: Visitors give good reviews to this Shepherdstown vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Shepherdstown?

Expedia has 10 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 Shepherdstown Public Library 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.