Shepherdstown Vacations from $359

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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.
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 $555, price is now $359 per person
$359
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
6/10 (1 review)
Residence Inn by Marriott Washington, DC National Mall

Residence Inn by Marriott Washington, DC National Mall

3 out of 5
Southwest
Save 100% on your flight
Price was $1,216, price is now $730 per person
$730
per person
Jul 27 - Jul 30
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Clean, safe, walkable, helpful and friendly staff. Very nice, spacious one bedroom suite. The free breakfast is one of the best I've ever seen.

Reviewed on Jun 25, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $634, price is now $402 per person
$402
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,022 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $642, price is now $412 per person
$412
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (2,770 reviews)
Bar and staff were nice. Multiple elevators were down when we visited making checkout time chaotic. Elevators only take 6 ppl, especially when Multiple events where happening in the area. Couldn't take the stairs because they were closed. It was about 30 minutes. The bathtubs needed scrubbing. Use to love staying here years ago but feels like the upkeep has changed.

Reviewed on Jun 24, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,002, price is now $653 per person
$653
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.6/10 Exceptional! (75 reviews)
Loved our time here - will definitely be coming back

Reviewed on Jun 22, 2026

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Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/5 (1 review)
This intimate historic theater hosts diverse performances from indie films to live music in a beautifully preserved setting. Arrive early to enjoy Shepherdstown's dining scene before your show.
See properties

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
$87 nightly
The price is $97 total per night from Jul 26 to Jul 27
$97 total
Jul 26 - Jul 27
Total with taxes and fees
8/10 Very Good! (256 reviews)
"The room was clean and comfortable. Great price!"

Reviewed on Jun 25, 2026

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
$123 nightly
The price is $137 total per night from Jul 9 to Jul 10
$137 total
Jul 9 - Jul 10
Total with taxes and fees
9.6/10 Exceptional! (78 reviews)
"Cute and quiet place to stay. It was clean and did what it had to for our 3 night stay!"

Reviewed on Jun 11, 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
Fully refundable
$100 nightly
The price is $112 total per night from Jul 26 to Jul 27
$112 total
Jul 26 - Jul 27
Total with taxes and fees
8.6/10 Excellent! (1,296 reviews)
"Clean, quiet, comfy bed…would definitely stay there again!"

Reviewed on Jun 25, 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 949 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 $359 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.