Shepherdstown Vacation Packages 2025/2026 from $291

Shepherdstown flight + hotel vacation packages

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

Hampton Inn & Suites Baltimore Inner Harbor

Downtown Baltimore

Save 100% on your flight

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Enjoy the free buffet breakfast each morning.

Hamilton Hotel Washington DC

Downtown Washington D.C.

Save 100% on your flight

per person

Sep 24 - Sep 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a terrace and multilingual staff can provide around-the-clock assistance.

The St. Gregory Hotel

Downtown Washington D.C.

Save 100% on your flight

per person

Oct 23 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Washington (DCA)

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

Hotel Ulysses, a Member of Design Hotels

Mount Vernon

Save 100% on your flight

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop, a snack bar/deli, and dry cleaning are also on offer.

Hotel Indigo Baltimore Downtown by IHG

Mount Vernon

Save 100% on your flight

per person

Nov 5 - Nov 9

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 business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and a grocery/convenience store are also offered.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr, Shepherdstown, WV

Free Cancellation

$96 nightly

$108 total

Sep 7 - Sep 8

Total includes taxes and fees

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

❤️ Secluded 1940s Romantic Tiny House on the River

$129 nightly

$143 total

Sep 1 - Sep 2

Total includes taxes and fees

This cabin includes a garden and barbecue grills.

Free WiFi

Air conditioning

Country Inn & Suites by Radisson, Frederick, MD

5579 Spectrum Dr, Frederick, MD

Free Cancellation

$85 nightly

$94 total

Aug 18 - Aug 19

Total includes 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

Hilton Garden Inn Frederick

7226 Corporate Ct, Frederick, MD

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$112 total

Aug 17 - Aug 18

Total includes taxes and fees

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

Tru By Hilton Martinsburg

801 Snapp Street, Martinsburg, WV

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$114 total

Aug 24 - Aug 25

Total includes taxes and fees

A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Express check-out is provided and the front desk is staffed around-the-clock.

Breakfast included

Pet friendly

Quality Inn

25 Union St, Harpers Ferry, WV

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$90 total

Aug 24 - Aug 25

Total includes taxes and fees

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

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

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

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?

$291 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.