Shepherdstown Vacation Packages 2025/2026 from $346

Shepherdstown flight + hotel vacation packages

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

InterContinental Washington D.C. - The Wharf by IHG

The Wharf

$346

per person

Dec 23 - Dec 28

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.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

$591

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

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.

Washington Hilton

Northwest

Save 100% on your flight

$454

per person

Jan 4 - Jan 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

This hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Beacon Hotel & Corporate Quarters

Downtown Washington D.C.

Save 100% on your flight

$402

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A 24-hour gym, valet parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the business center and free internet in public areas.

Club Quarters Hotel in Washington DC

Downtown Washington D.C.

Save 100% on your flight

$431

per person

Jan 11 - Jan 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Washington (DCA)

A 24-hour gym is featured at this hotel, along with free WiFi in public areas and a communal living room. Business travelers can take advantage of the business center. Express check-in, express check-out, and a computer station are also on offer.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr, Shepherdstown, WV

Free Cancellation

$90 nightly

$101 total

Nov 23 - Nov 24

Total with 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

$95 nightly

$105 total

Nov 18 - Nov 19

Total with 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

$80 nightly

$89 total

Dec 1 - Dec 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

Hilton Garden Inn Frederick

7226 Corporate Ct, Frederick, MD

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$93 total

Nov 24 - Nov 25

Total with 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

Clarion Inn Harpers Ferry - Charles Town

4328 William L Wilson Fwy, Harpers Ferry, WV

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Nov 23 - Nov 24

Total with taxes and fees

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

Days Inn by Wyndham Frederick

5646 Buckeystown Pike, Frederick, MD

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$70 total

Nov 20 - Nov 21

Total with taxes and fees

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

Pool

Breakfast 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?

$346 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.