Shepherdstown Vacations from $184
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Your Shepherdstown Vacation
When you choose a Shepherdstown vacation package, you can really enjoy your adventure to the fullest. Delve into the highlights of this fascinating city knowing that all your travel needs have been taken care of in advance. You'll want to take in the sights during your trip to Shepherdstown. Carve out some time for popular attractions like Antietam National Battlefield, Shepherd University and Antietam National Cemetery. Whatever your travel plans or the size of your budget, organizing a tailored Shepherdstown vacation is a breeze with Expedia.
The Latest Shepherdstown vacation packages
Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
Northeast
$231
per person
Nov 6 - Nov 9
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,005 reviews)
It was clean and very comfortable. It was also good convenient location close to everything by drive.
Reviewed on Sep 12, 2026
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View all tripsStay near popular Shepherdstown attractions
Shepherdstown Opera House
10.0/10 (1 review)
This intimate historic theater hosts diverse performances from indie films to live music in a beautifully preserved setting. Arrive early to enjoy Shepherdstown's dining scene before your show.
Shepherdstown Historic District
Wander through America's oldest West Virginia town, where 18th-century architecture tells stories from the 1730s. Explore German Street's unique shops and historic venues like the Shepherdstown Opera House.
Shepherdstown City Hall
This historic building serves as the administrative heart of Shepherdstown's charming historic district. Admire its regional architectural style while exploring nearby heritage sites and local shops.
Scarborough Library
Scarborough Library houses over 158,000 volumes and serves as Shepherd University's academic heart. Its solar-paneled roof showcases the institution's commitment to sustainability while providing a research space.
Rumsey Steamboat Museum
2.0/10 (1 review)
This intimate museum showcases James Rumsey's revolutionary 1787 steamboat, predating Fulton by decades. Explore the working replica and a vivid historical mural depicting the original Potomac River demonstration.
Shepherdstown Museum
8.0/10 (1 review)
Housed in the historic Entler Hotel, this museum showcases Shepherdstown's rich past through local artifacts and documents. The James Rumsey Boathouse features a working replica of the inventor's pioneering steamboat.
Ram Stadium
Catch an event at Ram Stadium during your trip to Shepherdstown. While you're in the area, stroll along the riverfront.
Morgan's Grove Park
This peaceful 20-acre park offers walking trails, sports fields, and a spring-fed stream amid mature trees. Enjoy a picnic in the shade or let children explore the playgrounds in this local West Virginia retreat.
What to do in Shepherdstown
Shepherdstown Hotel Deals
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
$105 nightly
$118 total
Oct 4 - Oct 5
Total with taxes and fees
8/10 Very Good! (317 reviews)
"The room seemed clean at check in. However the water pressure in the sink was very low and the tub didn’t drain while showering. As we went right to bed we didn’t notice much else. In the morning (and we had no exposed food with us) the entire table and tv dresser was covered with ants. Upon checkout ..."
Reviewed on Sep 12, 2026
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
$99 nightly
$110 total
Oct 5 - Oct 6
Total with taxes and fees
9.6/10 Exceptional! (85 reviews)
"I absolutely enjoyed my stay at the Stone Cottage. It was exactly what I was looking for—a quiet, peaceful solo getaway with no distractions and plenty of space to simply relax and enjoy being alone. The property was just as described and provided the perfect setting for some much-needed quiet time.The ..."
Reviewed on Sep 12, 2026
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
$109 nightly
$122 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Very clean and quiet. The breakfast was good also"
Reviewed on Sep 12, 2026
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.
Find the Best Shepherdstown Vacation Packages
Shepherdstown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Hagerstown Regional Airport (HGR) |
Population | 2,100 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Bolivar Heights Scenic Overlook, Shepherdstown Museum and John Browns Fort |
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Frequently asked questions
How much does a Shepherdstown vacation package cost?
You'll find cheap prices from $184 on Expedia for your Shepherdstown getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Shepherdstown costs.
What are the cheapest months to go to Shepherdstown?
If you'd like to score a cheap Shepherdstown vacation package, consider traveling in November, December and January. You'll usually find lower rates on airfares and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Shepherdstown?
Generally, a handful of days is enough to tick off the major attractions during your Shepherdstown vacation. However, if you prefer to have some time to chill out or take day tours, consider extending your itinerary.
Is it worth booking a vacation package to Shepherdstown?
Shepherdstown offers everything you need for a wonderful trip. Begin your Shepherdstown vacation on a high note by visiting top attractions like Shepherdstown Visitors Center.
How to find the best Shepherdstown package deals?
Begin your search for a Shepherdstown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shepherdstown package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Shepherdstown escape off to a flying start.
Is it cheaper to book a Shepherdstown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Shepherdstown vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Shepherdstown?
Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Shepherdstown break.
Does Expedia offer Book Now, Pay Later Shepherdstown vacation packages?
Set off on your perfect trip to Shepherdstown with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.