Shepherdstown Vacations from $266

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Your Shepherdstown Vacation

When you choose a Shepherdstown vacation 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, organizing a tailored Shepherdstown vacation is a breeze with Expedia.

The Latest Shepherdstown vacation packages

Price found within the past 48 hours. Click for updated prices.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $397, price is now $266 per person
$266
per person
Jun 7 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
The room pictures online don't quite do it justice! They are really beautiful, modern, spacious with incredible beddings. Loved it! It's easy to do ride share or walk to nearby restaurants and sights. The staff is very helpful!

Reviewed on Apr 12, 2026

Marriott Marquis Washington, DC

Marriott Marquis Washington, DC

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $575, price is now $320 per person
$320
per person
Jul 1 - Jul 4
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,005 reviews)
Lovely hotel experience with the kindest staff.

Reviewed on Apr 12, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $2,309, price is now $1,534 per person
$1,534
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,417 reviews)
We had a great stay! Positives: Friendly staff, comfortable room and bed, nice shower. Things that need work: Electical in our room had issues, fridge and coffee didn’t work first day. Internet is slow and had streaming issues trying to use Netflix.

Reviewed on Apr 12, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $486, price is now $325 per person
$325
per person
Jun 18 - Jun 22
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
No reviews
Residence Inn Alexandria Old Town South at Carlyle

Residence Inn Alexandria Old Town South at Carlyle

3 out of 5
Eisenhower East
Save 100% on your flight
Price was $1,112, price is now $743 per person
$743
per person
Jun 28 - Jul 5
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Tip—park at lot next to Eisenhower metro station 8 daily vs 40 daily at hotel.5 min walk Place is close to metro and free dash buses

Reviewed on Apr 7, 2026

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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

What to do in Shepherdstown

South Mountain Private Battlefield Tour

South Mountain Private Battlefield Tour

$120
per traveler
South Mountain Private Battlefield Tour
See all activities in Shepherdstown

Shepherdstown Hotel Deals

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
$120 nightly
The price is $133 total per night from Apr 20 to Apr 21
$133 total
Apr 20 - Apr 21
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
Fully refundable
$84 nightly
The price is $94 total per night from Apr 23 to Apr 24
$94 total
Apr 23 - Apr 24
Total with taxes and fees
7.8/10 Good! (222 reviews)
It's a nice inn, people are rather friendly, and the breakfast items are pretty much what you expect at a Quality Inn. The biggest issue was that the entire property is infested with ants - they are everywhere - in the room, bathroom, and dining area. The management needs to address it asap. As of ...

Reviewed on Apr 2, 2026

Quality Inn Shepherdstown
Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub

Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub

Shepherdstown WV
10/10 Exceptional! (1 review)
Beautiful area!

Reviewed on Sep 1, 2025

Get rates
Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub
See all 965 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.

Find the Best Shepherdstown Vacation Packages

Shepherdstown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hagerstown Regional Airport (HGR)
Population
2,100
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Bolivar Heights Scenic Overlook, Shepherdstown Museum and John Browns Fort

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Frequently asked questions

How much does a Shepherdstown vacation package cost?
You'll find cheap prices from $266 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?
If you'd like to score a cheap Shepherdstown vacation package, consider traveling in November, December and January. You'll usually find lower rates on airfares and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Shepherdstown?
Generally, a handful of days is enough to tick off the major attractions during your Shepherdstown vacation. However, if you prefer to have some time to chill out or take day tours, consider extending your itinerary.
Is it worth booking a vacation package to Shepherdstown?
Shepherdstown offers everything you need for a wonderful trip. Begin your Shepherdstown vacation on a high note by visiting top attractions like Shepherdstown Visitors Center.
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.
Does Expedia offer Book Now, Pay Later Shepherdstown vacation packages?
Set off on your perfect trip to Shepherdstown with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.

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