Shepherdstown Vacations from $282
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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
$546
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,004 reviews)
I love that it’s located on university campus, great for family bringing students from out of state.
Reviewed on Aug 5, 2026
The River Inn
Northwest
$382
per person
Oct 9 - Oct 12
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,056 reviews)
Great location. Super friendly staff. Huge room. Perfect for traveling with little ones who need space ans flexibility.
Reviewed on Aug 7, 2026
Hotel Burg
Leesburg's Old and Historic District
$1,034
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.6/10 Exceptional! (100 reviews)
Excellent service and hospitality. Beautiful and clean. Would come back here many times. Friendly and professional staff. It was a great experience.
Reviewed on Aug 4, 2026
Furnished Apartments
Ashton Heights
$745
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
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View all tripsStay near popular Shepherdstown attractions
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 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 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.
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.
Rumsey Monument
This 75-foot stone tribute honors James Rumsey, who demonstrated a steamboat in 1787, predating Fulton's famous vessel. From its hilltop perch, enjoy sweeping views of the Potomac River and Blue Ridge Mountains.
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.
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.
Bane Harris Community Park
Bane Harris Community Park is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.
What to do in Shepherdstown
Shepherdstown Hotel Deals
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
$95 nightly
$107 total
Aug 30 - Aug 31
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
$127 nightly
$141 total
Aug 31 - Sep 1
Total with taxes and fees
9.8/10 Exceptional! (82 reviews)
"This is a nice secluded place to unwind."
Reviewed on Jul 23, 2026
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
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 $282 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.
Explore a world of travel with Expedia
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- Visit Charles Town
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- Beall Air
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
