Shepherdstown Vacations

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Find the Best Shepherdstown Vacation Packages

Shepherdstown Hotel Deals

❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
The price is AED 257 per night from Mar 18 to Mar 19
AED 257
AED 510 total
includes taxes & fees
18 Mar - 19 Mar
9.8/10 Exceptional! (51 reviews)
Lovely stay!
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been ..."

Reviewed on 29 January 2025

❤️ Secluded 1940s Romantic Tiny House on the River
Charming Cabin in the Woods with River Access
Charming Cabin in the Woods with River Access
Shepherdstown
9.6/10 Exceptional! (17 reviews)
Great get-away spot!
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful ..."

Reviewed on 30 January 2025

Get rates
Charming Cabin in the Woods with River Access
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 AED 298 per night from Mar 24 to Mar 25
AED 298
AED 331 total
includes taxes & fees
24 Mar - 25 Mar
8.4/10 Very Good! (1,005 reviews)
"Friendly staff, very welcoming. Clean room. Great experience."

Reviewed on 3 March 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 820 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.

Frequently asked questions

How much does a Shepherdstown vacation 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 vacation 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 vacation packages. Keep in mind that public holidays and local events and festivals can impact prices, so do your research before booking.
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.
How to plan a trip to Shepherdstown?

  1. Choose your dates: What you’d like to do in Shepherdstown and your favorite 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 personalized Shepherdstown vacation package.

Discover the most popular places to visit in Shepherdstown

Shepherd University

4.5/5(5 reviews)

Explore the campus of Shepherd University, during your travels in Shepherdstown. Amble around the area's riverfront, or seek out its horseback riding.

Shepherd University

Shepherdstown Visitors Center

4/5(1 review)

Shepherdstown Visitors Center is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? Amble around the area's riverfront, or seek out its horseback riding.

Shepherdstown Visitors Center

Shepherdstown Opera House

5/5(1 review)

Enjoy a performance at Shepherdstown Opera House, a theater with a story to tell in Shepherdstown. Stroll along the riverfront or seek out the horseback riding.

Shepherdstown Opera House