Shepherdstown Vacations from $309

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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 $530, price is now $309 per person
$309
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,099 reviews)
Wanda at the front desk was very welcoming and helpful. The hotel doesn't have a restaurant and the complimentary breakfast is substandard. Glad food delivery was available. There isnt much in the immediate area that is available unless you have a car. Going forward I won't be staying as I prefer being closer to downtown DC

Reviewed on Oct 18, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was $844, price is now $351 per person
$351
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,022 reviews)
I had a nice room with a comfortable bed and a good view

Reviewed on Oct 18, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $901, price is now $433 per person
$433
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.6/10 Exceptional! (65 reviews)
I would give this property five stars, except for the extremely poor water pressure in the shower. It also did not get very hot. The staff and all the other amenities were excellent!

Reviewed on Oct 15, 2025

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Save 100% on your flight
Price was $613, price is now $366 per person
$366
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,020 reviews)
Everything went as planned

Reviewed on Oct 15, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,230, price is now $736 per person
$736
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,074 reviews)
The happy hour is fantastic, and the location is excellent. The staff is friendly, especially the overnight valet.specially the overnight valet.

Reviewed on Oct 14, 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

Shepherdstown Hotel Deals

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
Fully refundable
$91 nightly
The price is $102 total per night from Nov 2 to Nov 3
$102 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (184 reviews)
"Clean room. Great parking. Good place to stay on a budget."

Reviewed on Oct 16, 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
$85 nightly
The price is $95 total per night from Nov 18 to Nov 19
$95 total
Nov 18 - Nov 19
Total with taxes and fees
8.2/10 Very Good! (1,148 reviews)
"The place was clean, comfortable and quiet."

Reviewed on Oct 12, 2025

Country Inn & Suites by Radisson, Frederick, MD
Quality Inn

Quality Inn

2.5 out of 5
25 Union St, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $98 total per night from Oct 26 to Oct 27
$98 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"On the Appalachian Trail, staff is kind and helpful."

Reviewed on Oct 11, 2025

Quality Inn
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.

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 $309 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.