Shepherdstown Vacations from ￥151,011

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The Latest Shepherdstown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eaton DC

Eaton DC

4.5 out of 5
Downtown Washington D.C.
Price was ￥170,615, price is now ￥151,011 per person
￥151,011
per person
Oct 28 - Oct 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.2/10 Wonderful! (1,406 reviews)
Great old school hotel with modern touches

Reviewed on Aug 24, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Price was ￥229,975, price is now ￥191,233 per person
￥191,233
per person
Oct 28 - Oct 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.4/10 Exceptional! (1,002 reviews)
On arrival lights didn’t work. Moved to another room next day, couldn’t fault it, view of Jefferson Memorial (as requested) higher floor & fizz, cake & hand made chocolates left in room. Very friendly reception, housekeeping & room service. Excellent breakfast (complimentary on first morning for inconvenience on arrival) delicious & service in all areas exceptional. Thank you Eskadar for looking after us

Reviewed on Aug 23, 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Price was ￥184,400, price is now ￥156,694 per person
￥156,694
per person
Oct 28 - Oct 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.2/10 Wonderful! (836 reviews)
Loved the location and cleanliness. Rooftop bar overall had a rude experience. Not very friendly bartenders. Not a large selection of alcohol if you are on vacation.

Reviewed on Aug 24, 2025

Viceroy Washington DC

Viceroy Washington DC

4.5 out of 5
Downtown Washington D.C.
Price was ￥178,861, price is now ￥156,508 per person
￥156,508
per person
Oct 28 - Oct 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.4/10 Exceptional! (1,012 reviews)
Very nice and amiable stay. A very comfortable room.

Reviewed on Aug 25, 2025

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Price was ￥176,562, price is now ￥156,107 per person
￥156,107
per person
Oct 28 - Oct 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.4/10 Exceptional! (2,226 reviews)
close to the train station, staff extremely nice and clean rooms.

Reviewed on Aug 24, 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 ￥13,989 per night from Sep 21 to Sep 22
￥13,989
￥15,667 total
Sep 21 - Sep 22
includes taxes & fees
7.6/10 Good! (164 reviews)
"The only 2 issues were that breakfast could if been better by having more options for breakfast and they don't have ice machines however they have ice buckets with bags in rooms???¡!"

Reviewed on Aug 25, 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is ￥9,786 per night from Sep 1 to Sep 2
￥9,786
￥19,837 total
Sep 1 - Sep 2
includes taxes & fees
9.8/10 Exceptional! (60 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 Aug 3, 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 ￥13,277 per night from Sep 3 to Sep 4
￥13,277
￥14,738 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,090 reviews)
"The hotel is quite and clean."

Reviewed on Aug 21, 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 895 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 ￥151,011 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.