Shepherdstown Holidays
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Top Flight + Hotel Deals in Shepherdstown
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
€1,487
per person
15 Sept - 21 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
I had a family emergency and asked the front desk if I could have a refund even though I was there for about 2 hours. They said they would definitely look into it. I’ve tried contacting them repeatedly but have not received any response.
Reviewed on 14 Aug 2026
The William Fell Baltimore, Tapestry Collection by Hilton
Fells Point
€1,777
per person
15 Sept - 21 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9.2/10 Wonderful! (238 reviews)
Location was amazing and the hotel was very clean and staff was great. You can’t find a better location
Reviewed on 11 Aug 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
€1,519
per person
15 Sept - 21 Sept
found 6 hours ago
Return flight included
Dublin (DUB) to Baltimore (BWI)
9.2/10 Wonderful! (835 reviews)
The evening I checked in, your front desk man: Eric was friendly and extremely helpful. The room was spotless and the beds were amazingly comfortable. I will recommend this hotel to friends and family. 2 thumbs up, get adventurous fun!
Reviewed on 13 Aug 2026
Top hotels in Shepherdstown
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
€98
13 Sept - 14 Sept
includes taxes & fees
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
€126
7 Sept - 8 Sept
includes taxes & fees
9.8/10 Exceptional! (82 reviews)
"This is a nice secluded place to unwind."
Reviewed on 23 Jul 2026
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
€100
13 Sept - 14 Sept
includes taxes & fees
8.6/10 Excellent! (1,307 reviews)
"Closed, had to book another hotel Hopefully I can get my money back"
Reviewed on 14 Aug 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.
Stay 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 Museum
8.0/10 (1 review)
Housed in the historic Entler Hotel, this museum showcases Shepherdstown's rich past through local artefacts and documents. The James Rumsey Boathouse features a working replica of the inventor's pioneering steamboat.
Shepherdstown Opera House
10.0/10 (1 review)
This intimate historic theatre 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.
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.
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.
Rumsey Monument
This 75-foot stone tribute honours 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.
Frequently asked questions
How much does a Shepherdstown holiday package cost?
You'll find cheap prices from €1,487 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 holiday to Shepherdstown costs.
What are the cheapest months to go to Shepherdstown?
Plan your getaway for the low season and you're likely to score cheap Shepherdstown holiday packages. Keep in mind that public holidays and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Shepherdstown?
With a well-organised itinerary, you can easily hit the most popular Shepherdstown sights in a few days. But if you want to explore off the beaten track or go on day tours, think about booking your Shepherdstown holiday for longer.
Is it worth booking a holiday package to Shepherdstown?
It's easy to see why a Shepherdstown holiday is on the must-do list of many travellers. Popular attractions like Shepherdstown Visitors Centre are just the beginning of what you can explore here.
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 holiday as a package?
Expedia holiday 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 customised Shepherdstown holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Shepherdstown?
- Choose your dates: What you'd like to do in Shepherdstown and your favourite season can help you decide when to go.
- Plan your budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Shepherdstown.
- Decide how long to go away for: Now that you're more familiar with Shepherdstown, you can work out the right length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Shepherdstown holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
