Shepherdstown Vacations from ￥209,737

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Shepherdstown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.8/10 Excellent! (2,464 reviews)
Clean, excellent quality, friendly stuff. Restaurant is of an excellent quality, although maybe a little more expensive that I would expect. Good location for the purpose of my visit. Relatively far from the subway stations though; however buses are coming near.

Reviewed on Jun 19, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Aug 21 - Aug 27
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
Beautiful Property. Amazing Dinner options. Super friendly and professional staff willing to help anytime.

Reviewed on Jun 19, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Aug 21 - Aug 27
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (HND) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Great hotel walking distance from the national mall! Only wished our room hsd a microwave, otherwise it was a great value. Would stay here again.

Reviewed on Jun 16, 2025

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
Never a disappointment. Staff are friendly and helpful. Everything is well taken care of.

Reviewed on Jun 9, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.8/10 Excellent! (1,003 reviews)
Great location, upscale luxurious room and great service

Reviewed on Jun 20, 2025

Find the Best Shepherdstown Vacation Packages

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 ￥11,052 per night from Jul 6 to Jul 7
￥11,052
￥12,378 total
Jul 6 - Jul 7
includes taxes & fees
7.6/10 Good! (136 reviews)
Did the job
"The manager went out of his way to make us feel welcome. Room was fine and breakfast spartan but serviceable."

Reviewed on Jun 14, 2025

Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
The price is ￥9,993 per night from Jul 2 to Jul 3
￥9,993
￥20,015 total
Jul 2 - Jul 3
includes taxes & fees
9.8/10 Exceptional! (56 reviews)
"We truly loved this location and definitely will be back!"

Reviewed on May 25, 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 ￥11,302 per night from Jul 2 to Jul 3
￥11,302
￥12,545 total
Jul 2 - Jul 3
includes taxes & fees
8.2/10 Very Good! (1,014 reviews)
"The room wasn’t very clean."

Reviewed on Jun 17, 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 879 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 from ￥209,737 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 many days is enough for Shepherdstown?
With a well-organized 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 vacation for longer.
Is it worth booking a vacation package to Shepherdstown?
It's easy to see why a Shepherdstown vacation is on the must-do list of many travelers. Popular attractions like Shepherdstown Visitors Center 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.