Shepherdstown Vacation Packages 2026 from $387

Shepherdstown flight + hotel vacation packages

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

YOTEL Washington DC

Northwest

$387

per person

Mar 28 - Mar 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll appreciate the seasonal outdoor pool, poolside bar, and concierge services.

Hampton Inn & Suites Washington DC-Navy Yard

Navy Yard

Save 100% on your flight

$388

per person

Mar 27 - Mar 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the a rooftop terrace and free buffet breakfast each morning.

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$1,092

per person

Apr 16 - Apr 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.

Global Luxury Suites at The White House

Downtown Washington D.C.

Save 100% on your flight

$1,021

per person

Mar 20 - Mar 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This aparthotel features a 24-hour gym and a rooftop terrace. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.

InterContinental Washington D.C. - The Wharf by IHG

Southwest

Save 100% on your flight

$539

per person

Mar 28 - Mar 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr Shepherdstown WV

Free Cancellation

$77 nightly

$87 total

Feb 22 - Feb 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV

$95 nightly

$105 total

Feb 23 - Feb 24

Total with taxes and fees

This cabin includes a garden and barbecue grills.

Hampton Inn Martinsburg

975 Foxcroft Ave Martinsburg WV

Free Cancellation

Reserve now, pay when you stay

$86 nightly

$97 total

Feb 17 - Feb 18

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Country Inn & Suites by Radisson, Frederick, MD

5579 Spectrum Dr Frederick MD

Free Cancellation

$77 nightly

$85 total

Feb 27 - Feb 28

Total with taxes and fees

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.

Country Inn & Suites by Radisson, Hagerstown, MD

17612 Valley Mall Rd Hagerstown MD

Free Cancellation

$85 nightly

$95 total

Mar 2 - Mar 3

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

SpringHill Suites by Marriott Frederick

111 Byte Drive Frederick MD

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$109 total

Feb 17 - Feb 18

Total with taxes and fees

This hotel features an indoor pool and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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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 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 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.

Frequently asked questions

How much are vacation packages to Shepherdstown?

$387 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.