Shepherdstown Vacation Packages 2026 from $489

Shepherdstown flight + hotel vacation packages

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

Kimpton Banneker Hotel by IHG

Downtown Washington D.C.

$489

per person

Jul 30 - Aug 2

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 laundry service, conference space, and valet parking. A communal living room, luggage storage, and concierge services are also on offer.

Hotel Rendale Washington DC

Northwest

Save 100% on your flight

$527

per person

Jun 27 - Jul 1

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a coffee shop, and a terrace are also offered.

The Waypoint

West Rehoboth

Save 100% on your flight

$882

per person

Jul 27 - Aug 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This hotel doesn't skimp on freebies - guests have free WiFi and a free bus station shuttle. Luggage storage and a virtual front desk are also provided.

Club Wyndham National Harbor

Save 100% on your flight

$573

per person

Jul 24 - Jul 27

just found

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

2 hot tubs, an indoor pool, and a 24-hour gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free WiFi.

Rosewood Washington, D.C.

Northwest

Save 100% on your flight

$1,152

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

The aparthotel's outdoor pool, indoor pool, and 2 bars/lounges are among the featured amenities. Families will appreciate complimentary bicycles and in-room childcare. Enjoy the 24-hour gym and perks like free WiFi.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr Shepherdstown WV

Free Cancellation

$94 nightly

$105 total

Jun 1 - Jun 2

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

$122 nightly

$135 total

May 19 - May 20

Total with taxes and fees

This cabin includes a garden and barbecue grills.

Free WiFi

Air conditioning

Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub

Shepherdstown WV

Get rates

This castle features a gym and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Hot Tub

Air conditioning

Hampton Inn Martinsburg

975 Foxcroft Ave Martinsburg WV

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$110 total

May 24 - May 25

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

$91 nightly

$101 total

Jun 1 - Jun 2

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.

Breakfast included

Pet friendly

Fairfield Inn & Suites by Marriott Hagerstown

89 ALL STAR COURT Hagerstown MD

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$122 total

May 17 - May 18

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Pool

Breakfast included

Don't see what you're looking for?

See all available properties in Shepherdstown

View all properties

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?

$489 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.