Shepherdstown Vacation Packages 2026 from $310

Shepherdstown flight + hotel vacation packages

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

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$310

per person

Nov 5 - Nov 8

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

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.

The Poppy Georgetown

Northwest

$830

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This hotel features 2 outdoor tennis courts and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free continental breakfast each morning.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

$674

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

A restaurant and a bar/lounge are featured at this hotel. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$315

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$760

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr Shepherdstown WV

Free Cancellation

$101 nightly

$113 total

Sep 20 - Sep 21

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.

Breakfast included

Pet friendly

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV

$120 nightly

$133 total

Sep 7 - Sep 8

Total with taxes and fees

This cabin includes a garden and barbecue grills.

Country Inn & Suites by Radisson, Hagerstown, MD

17612 Valley Mall Rd Hagerstown MD

Free Cancellation

$99 nightly

$111 total

Sep 3 - Sep 4

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.

Country Inn & Suites by Radisson, Frederick, MD

5579 Spectrum Dr Frederick MD

Free Cancellation

$85 nightly

$95 total

Sep 27 - Sep 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.

Hampton Inn Martinsburg

975 Foxcroft Ave Martinsburg WV

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$116 total

Sep 4 - Sep 5

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.

Pool

Breakfast included

The Plaza Inn & Suites

931 Dual Highway, Building A Hagerstown MD

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$78 total

Aug 30 - Aug 31

Total with taxes and fees

An indoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pool

Pet friendly

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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.

Stay near popular Shepherdstown attractions

Shepherdstown Historic District

Find out about the history of Shepherdstown when you take a trip to Shepherdstown Historic District. While you're in the area, stroll along the riverfront.

See properties

Frequently asked questions

How much are vacation packages to Shepherdstown?

$310 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.