Shepherdstown Vacation Packages 2026 from $480

Shepherdstown flight + hotel vacation packages

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

Hotel Hive

Northwest

Save 100% on your flight

$480

per person

Nov 2 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A terrace and luggage storage are also provided.

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.

Save 100% on your flight

$885

per person

Nov 2 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.

Save 100% on your flight

$578

per person

Nov 2 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

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.

InterContinental Washington D.C. - The Wharf by IHG

The Wharf

Save 100% on your flight

$956

per person

Nov 2 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

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.

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$1,152

per person

Oct 16 - Oct 19

found 17 hours ago

Roundtrip flight included

Dallas (DFW) 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

$106 nightly

$119 total

Oct 6 - Oct 7

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

$99 nightly

$110 total

Oct 5 - Oct 6

Total with taxes and fees

This cabin includes a garden and barbecue grills.

Free WiFi

Air conditioning

Quality Inn Harpers Ferry - Charles Town

25 Union St Harpers Ferry WV

Free Cancellation

$111 nightly

$124 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a gym and in-room fitness. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Breakfast included

Parking included

Best Western Historic Frederick

420 Prospect Blvd Frederick MD

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$104 total

Oct 8 - Oct 9

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.

Pool

Breakfast included

Fairfield Inn & Suites by Marriott Hagerstown

89 ALL STAR COURT Hagerstown MD

$101 nightly

$114 total

Oct 11 - Oct 12

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.

Comfort Inn Frederick - Ballenger Creek

7300 Executive Way Frederick MD

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$98 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and free newspapers.

Breakfast included

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 Visitors Center

8.8/10 (3 reviews)

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.

See properties

Frequently asked questions

How much are vacation packages to Shepherdstown?

$480 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.