Shepherdstown Holidays from £787
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Your Shepherdstown Holiday
When you choose a Shepherdstown holiday 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, organising a tailored Shepherdstown holiday is a breeze with Expedia.
Top Shepherdstown Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
£787
per person
6 Oct - 11 Oct
just found
Return direct flight included
London (LGW) 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
Phoenix Park Hotel
Northwest
£789
per person
6 Oct - 11 Oct
just found
Return direct flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (2,183 reviews)
Great property with a great location. Just a couple blocks from Union Station which includes the Metro with access to everything in DC and surrounding areas.
Reviewed on 14 Aug 2026
Shepherdstown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Hagerstown Regional Airport (HGR) |
Population | 2,100 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Greenbrier State Park, Big Cork Vineyards and Bolivar Heights Scenic Overlook |
Top hotels in Shepherdstown
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
£84
13 Sept - 14 Sept
includes taxes & fees
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
£107
14 Sept - 15 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
£85
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
Why should I book my Shepherdstown holiday with Expedia?
Choose Expedia to arrange your next big break easily and all in one convenient place. Our top tip for scoring a fabulous deal on a Shepherdstown retreat? Bundle your flights, accommodation and/or hire car into a package holiday. Then add a few exciting tours and activities. Most bookings also include flexible cancellation policies, so there's no need to worry if you have to switch up your travel agenda. Round-the-clock assistance with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Shepherdstown?
April, May and July are the busiest months in Shepherdstown, while November, December and January are generally quieter. With daytime average temperatures of 0ºC, January is the coolest period in Shepherdstown. The warmest time of year is July, when you can experience average temperatures of 24ºC during the day. Whatever the weather, you'll find loads to keep you busy here.
What is the top hotel for my holiday in Shepherdstown?
Create unforgettable memories in Shepherdstown by choosing Springhill Suites by Marriott Hagerstown as your home-away-from-home and gateway to fun and adventure.
How do I get a cheap holiday to Shepherdstown?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and hire cars — we've got it all. Choose the combination that suits your style and watch your savings grow. We know holidays are never a one-size-fits-all. That's why Expedia offers over 400 airlines and 321,000 properties globally, which lets you customise your Shepherdstown holiday your way. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Shepherdstown holiday?
With popular attractions such as Antietam National Battlefield and Shepherd University, a holiday in Shepherdstown is filled with exciting places to visit. Big Cork Vineyards and Antietam National Cemetery are a couple of other sights worth discovering.
What is the best area to stay in when on holiday in Shepherdstown?
Shepherdstown has lots of interesting places to see, like Shepherd University. Stay somewhere nearby and make sightseeing stress-free.
Do I need a visa for my Shepherdstown holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the reason for your visit, whether it be for work or holidays, will determine if you'll need a visa for Shepherdstown. Also make sure your passport is up to date and has at least six months validity remaining after your return date. Do all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Shepherdstown holiday?
Although everyone's fashion style differs, it can be useful to have a few guidelines for what kind of clothes to wear during your holiday in Shepherdstown. We recommend looking up style blogs before you leave for inspiration on fashion trends or dress codes. Daytime temperatures in January, Shepherdstown's coolest month, average 0ºC. July marks this city's warmest month when the average temperature reaches 24ºC. Our tip? Take the guesswork out of what to pack and check the local weather conditions.
What does an Expedia Shepherdstown holiday include?
With Expedia, you can select a combination of hotels, flights and car hires to create your perfect Shepherdstown package. Once you've made your booking, simply add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the more cash you'll save! Expedia features different types of properties, with the most sought after in Shepherdstown including private holiday homes and cottages. With Expedia, you'll always have the flexibility and freedom to tailor your holiday any way you want.
Does Expedia offer Book Now, Pay Later Shepherdstown holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:
- Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
- No-deposit holidays: Hitting the "book now" button is much easier with this plan. With no upfront fee for your holiday, you can Book Now, Pay Later and get on your way.
Can I choose my airline with a Shepherdstown Expedia holiday?
Yes — that's one of the best things about an Expedia holiday package. You're the boss! We have access to more than 400 partner airlines throughout the world, so you have lots of choice when planning your Shepherdstown escape.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
