Shepherdstown Vacation Packages 2025 from $238

Shepherdstown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Arboretum

Northeast

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 4 onsite conference rooms. A gym is on site, and self parking and a 24-hour front desk are also offered.

SIXTY DC

Downtown Washington D.C.

Save 100% on your flight

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking is offered and the front desk is staffed around-the-clock.

DoubleTree by Hilton Washington DC North/Gaithersburg

Save 100% on your flight

per person

Jul 7 - Jul 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Hilton Garden Inn Baltimore/White Marsh

Nottingham

Save 100% on your flight

per person

Jul 7 - Jul 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the mini golf and barbecue grills. Enjoy the 24-hour gym and perks like free self parking and free WiFi.

DoubleTree Hotel Baltimore - BWI Airport

Save 100% on your flight

per person

Aug 6 - Aug 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the seasonal outdoor pool and perks like free self parking and a free area shuttle.

Top Shepherdstown hotels deals

❤️ Secluded 1940s Romantic Tiny House on the River

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This cabin includes a garden and barbecue grills.

Free WiFi

Air conditioning

Quality Inn Shepherdstown

70 Maddex Square Dr, Shepherdstown, WV

Free Cancellation

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This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free buffet breakfast each morning. A computer station and a safe deposit box are also provided.

Breakfast included

Pet friendly

Country Inn & Suites by Radisson, Frederick, MD

5579 Spectrum Dr, Frederick, MD

Free Cancellation

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This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Clarion Inn Harpers Ferry - Charles Town

4328 William L Wilson Fwy, Harpers Ferry, WV

Free Cancellation

Reserve now, pay when you stay

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A casino, a 24-hour gym, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Hilton Garden Inn Frederick

7226 Corporate Ct, Frederick, MD

Free Cancellation

Reserve now, pay when you stay

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Pool

Pet friendly

Quality Inn

25 Union St, Harpers Ferry, WV

Free Cancellation

Reserve now, pay when you stay

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This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Parking included

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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.

Popular places to visit

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.

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 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.

Frequently asked questions

How much are vacation packages to Shepherdstown?

$238 is all you need to spend for an unforgettable break in Shepherdstown. Bundle your hotel and flights into a Travelocity vacation package and see your savings grow. With these kinds of prices, you’ll want to start packing your bags now!

How long should my Shepherdstown vacation be?

Your Shepherdstown getaway can be as long or as short as you would like it to be, but the majority of travelers stay about 2 nights. Eager to venture out and uncover some less touristy sights? Stay a couple more nights and see a different side of this place.

Where can I get the best vacation package deals for Shepherdstown?

Your dream escape is waiting for you at Travelocity. With access to 400 airline partners and 1,000,000 properties across the globe, selecting the ultimate Shepherdstown package deal couldn’t be simpler.

Why should I book my Shepherdstown vacation package via Travelocity?

You’ll not only enjoy big savings, but you can also access our round-the-clock support, excellent service and a Price Match Guarantee. Wander across the world, uncover hidden treasures and forge long-lasting memories — we’ll take care of the important details.

Can I save on my Shepherdstown car rental if I book it with a hotel or flight?

Absolutely — combine your flight, hotel and car into a Shepherdstown vacation package and you can save a tidy sum. With so much to discover in and around Shepherdstown, that rental vehicle will make exploring easy. Once you’ve slid into the driver’s seat, put the stereo on and head toward White House, an unmissable sight about 55 mi from Shepherdstown.

Which airport is best for Shepherdstown?

Ronald Reagan Washington National Airport (DCA) (55 mi away from downtown), Washington Dulles Intl. Airport (IAD) (40 mi away from central Shepherdstown) and Hagerstown Regional Airport (HGR) (19 mi away from central Shepherdstown) are all top options for Shepherdstown.

What is there to do in Shepherdstown?

Shepherdstown is overflowing with sights to check out, like Shepherdstown Opera House and Shepherdstown Museum. These renowned attractions top most visitors’ must-see lists.

Where should I stay when visiting Shepherdstown?

If you’re looking for someplace comfortable to lay your head, check out the Bavarian Inn. It’s the top choice for many visitors.