Shepherdstown Holidays

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Your Shepherdstown Holiday

When you book a Shepherdstown holiday package, you can really enjoy your adventure to the fullest. Uncover the sights and sounds of this lively city knowing that everything has been taken care of in advance. Want to explore your surroundings? Shepherd University, Shepherdstown Opera House and Shepherdstown Museum are a few of the most popular places to visit during your trip to Shepherdstown. Whatever your travel plans or the size of your budget, putting together a tailored Shepherdstown holiday is easy with Expedia.

Shepherdstown Holiday

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
Big Cork Vineyards, Greenbrier State Park and Bolivar Heights Scenic Overlook

Our pick of the best Shepherdstown Hotel Deals

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
Fully refundable
The price is AU$167 per night from 7 Sept to 8 Sept
AU$167
7 Sept - 8 Sept
includes taxes & fees
7.6/10 Good! (161 reviews)
"Please step up the breakfast game, it is sub-par, and the coffee is not drinkable."

Reviewed on 17 Aug. 2025

Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is AU$214 per night from 2 Sept to 3 Sept
AU$214
2 Sept - 3 Sept
includes taxes & fees
9.8/10 Exceptional! (57 reviews)
"I left the children’s age for a purpose. Because y’all made us feel like we were high school kids again. Absolutely gorgeous views for a step up from tent camping. We will be back thank you"

Reviewed on 3 Aug. 2025

❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is AU$146 per night from 26 Aug to 27 Aug
AU$146
26 Aug - 27 Aug
includes taxes & fees
8.2/10 Very Good! (1,091 reviews)
"Friendly staff"

Reviewed on 20 Aug. 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 892 properties in Shepherdstown
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Shepherdstown holiday package cost?
You'll find cheap prices 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?

  1. Choose your dates: What you'd like to do in Shepherdstown and your favourite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.