Shepherdstown Vacations from $176

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $309, price is now $176 per person
$176
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,099 reviews)
IT WAS A VERY GOOD TIME FOR ME HAVE STIAD @ THE VIRGIN RIVER.AND THAT HOW WE'LL THEY TERIATED AND I WOULD LIKE TO KNOW HOW MUCH A ROOM.COSTS PER NIGHT

Reviewed on Nov 2, 2025

The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
Price was $1,039, price is now $642 per person
$642
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Washington (DCA)
8.6/10 Excellent! (1,663 reviews)
Always great service, smooth check-in and clean room

Reviewed on Nov 4, 2025

Courtyard by Marriott Baltimore Downtown/Inner Harbor

Courtyard by Marriott Baltimore Downtown/Inner Harbor

3 out of 5
Harbor East
Save 100% on your flight
Price was $504, price is now $317 per person
$317
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,006 reviews)
We were in an ajoining room suite on one side only. The bolt lock to the ajoining room was not locked nd could not be locked. Ajoining room was noisy until 11pm when we confronted them Bed mattress was very uncomfortable (hard and lumpy)

Reviewed on Oct 26, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $397, price is now $252 per person
$252
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (2,000 reviews)
Comfortable room. Friendly staff. Walking distance to nice shopping, yummy restaurants and the Capital One Center.

Reviewed on Nov 4, 2025

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $392, price is now $251 per person
$251
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,011 reviews)
Everything was perfect. Clean Room, Nice Staff and beautiful hotel.

Reviewed on Nov 3, 2025

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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 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

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

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

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
Fully refundable
$90 nightly
The price is $101 total per night from Nov 23 to Nov 24
$101 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (192 reviews)
The hotel staff was incredibly nice.

Reviewed on Oct 31, 2025

Quality Inn Shepherdstown
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
$77 nightly
The price is $85 total per night from Nov 24 to Nov 25
$85 total
Nov 24 - Nov 25
Total with taxes and fees
8.2/10 Very Good! (1,189 reviews)
Everything was beautiful and clean and great hospitality

Reviewed on Nov 3, 2025

Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Nov 24 to Nov 25
$93 total
Nov 24 - Nov 25
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Yes good staff.

Reviewed on Oct 30, 2025

Hilton Garden Inn Frederick
See all 940 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 $176 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.