Shepherdstown Vacation Packages 2026 from $466

Shepherdstown flight + hotel vacation packages

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

The Royal Sonesta Washington DC Dupont Circle

Northwest

Save 100% on your flight

$466

per person

Oct 25 - Oct 30

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 free WiFi in public areas, laundry service, and valet parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.

Save 100% on your flight

$530

per person

Oct 25 - Oct 30

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 express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

$833

per person

Oct 25 - Oct 30

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.

The River Inn

Northwest

Save 100% on your flight

$482

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

This aparthotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. A terrace, a free grocery shopping service, and a lobby fireplace are also on offer.

Lyle Washington D.C.

Northwest

Save 100% on your flight

$656

per person

Oct 25 - Oct 30

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. WiFi in public areas is free. Valet parking, a coffee shop, and a garden are also offered.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

70 Maddex Square Dr Shepherdstown WV

Free Cancellation

$99 nightly

$111 total

Sep 7 - Sep 8

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

$127 nightly

$141 total

Aug 31 - Sep 1

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

$110 nightly

$124 total

Sep 10 - Sep 11

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

$88 nightly

$98 total

Sep 6 - Sep 7

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

The Plaza Inn & Suites

931 Dual Highway, Building A Hagerstown MD

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$78 total

Aug 13 - Aug 14

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.

Best Western Historic Frederick

420 Prospect Blvd Frederick MD

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$91 total

Aug 24 - Aug 25

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, luggage storage, and laundry facilities are also on offer.

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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?

$466 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.