Shepherdstown Vacations from $196

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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.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was $488, price is now $196 per person
$196
per person
Jan 1 - Jan 4
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,022 reviews)
Everything was fantastic. Beautiful property.

Reviewed on Nov 10, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was $1,259, price is now $591 per person
$591
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9/10 Wonderful! (1,074 reviews)
Room was spotless and comfortable and quiet. All staff were very friendly and helpful. Great location to walk to the Metro and restaurants and the White House!

Reviewed on Oct 28, 2025

Kimpton Hotel Monaco Washington DC by IHG

Kimpton Hotel Monaco Washington DC by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $948, price is now $499 per person
$499
per person
Dec 26 - Jan 2
just found
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
8.4/10 Very Good! (1,004 reviews)
Clean room and friendly staff

Reviewed on Nov 2, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $450, price is now $240 per person
$240
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
8/10 Very Good! (1,099 reviews)
The room was clean and comfortable. The staff was very friendly and helpful. I felt safe there was security.

Reviewed on Nov 10, 2025

Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $707, price is now $402 per person
$402
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
7.6/10 Good! (1,027 reviews)
Room was clean, great location, wifi was too weak to get any work done

Reviewed on Nov 9, 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! (195 reviews)
Room was clean and beds comfy. Staff friendly Location Hotel was greatthe Hotel

Reviewed on Nov 6, 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
$95 nightly
The price is $105 total per night from Nov 18 to Nov 19
$105 total
Nov 18 - Nov 19
Total with taxes and fees
9.8/10 Exceptional! (63 reviews)
We had a lovely time at this sweet retreat! Everything as described and better! Would recommend:)

Reviewed on Oct 6, 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
$80 nightly
The price is $89 total per night from Dec 7 to Dec 8
$89 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (1,181 reviews)
The room was clean…bed was comfortable….

Reviewed on Nov 7, 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 903 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 $196 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.

Explore a world of travel with Expedia

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