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Shepherdstown flight + hotel packages

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The River Inn

The River Inn

4 out of 5
Northwest
Price was CA $1,189, price is now CA $845 per person
CA $845
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
Book a stay at this business-friendly aparthotel in Washington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Washington Monument are located nearby.
Residence Inn by Marriott Washington, DC National Mall

Residence Inn by Marriott Washington, DC National Mall

3 out of 5
Southwest
Price was CA $1,852, price is now CA $1,296 per person
CA $1,296
per person
Sep 22 - Sep 25
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions National Mall and Smithsonian Institution are located nearby.
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,441, price is now CA $1,750 per person
CA $1,750
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Stay at this hotel in Leesburg. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Popular attractions Gleedsville Art Gallery and Earth and Fire Gallery are located nearby.
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Price was CA $1,166, price is now CA $871 per person
CA $871
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Arlington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Arlington National Cemetery and Washington Monument are located nearby.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $1,580, price is now CA $1,187 per person
CA $1,187
per person
Sep 6 - Sep 10
found 15 hours ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.

Top Shepherdstown hotels deals

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
Free cancellation
The price is CA $141 per night
CA $141
CA $158 total
Aug 30 - Aug 31
includes taxes & fees
Stay at this hotel in Shepherdstown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maddex Square and Bane Harris Community Park are located nearby.
Breakfast included
Pet-friendly
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is CA $101 per night
CA $101
CA $198 total
Aug 31 - Sep 1
includes taxes & fees
Stay at this cabin in Shepherdstown. Enjoy free WiFi, a garden, and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
Free WiFi
Air conditioning
Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
Free cancellation
The price is CA $142 per night
CA $142
CA $159 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in Hagerstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Valley Mall and Regal Valley Mall are located nearby.
Pool
Breakfast included
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr Frederick MD
Free cancellation
The price is CA $121 per night
CA $121
CA $134 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Francis Scott Key Mall and Westview Promenade are located nearby.
The Plaza Inn & Suites

The Plaza Inn & Suites

2.5 out of 5
931 Dual Highway, Building A Hagerstown MD
Free cancellation
Reserve now, pay when you stay
The price is CA $88 per night
CA $88
CA $99 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this hotel in Hagerstown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hagerstown Field House and Maryland Theater are located nearby.
Pool
Pet-friendly
Best Western Historic Frederick

Best Western Historic Frederick

2.5 out of 5
420 Prospect Blvd Frederick MD
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $127 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Harry Grove Stadium and Baker Park are located nearby.
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.

Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/10 (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.
See properties

Shepherdstown Vacations

Experiencing the true essence of Shepherdstown begins with delving into a few basic facts. Are you ready to learn exactly where this unique destination is and which attractions you should explore?

From the heart of Martinsburg, you'll need to make your way east for 8 miles (13 kilometers) to get to this neighborhood.

At last count, the population of Martinsburg was 17,000.

Places to visit in Shepherdstown

Abandon your history books! See the past jump off the page at Shepherdstown Museum. Want more close by options? You don't need to know what chorus, cadenza or tenor mean to appreciate an evening out at the opera. Wear your best clothes and be hypnotized by heart-stopping performances and superb drama at Shepherdstown Opera House. And that's not all. Venturing out on the fairways is a great way to stretch your legs and have a real blast. Challenge your technique with a friendly round at Cress Creek Golf Club.

Where do you fly into for Shepherdstown?

If you're heading to Shepherdstown, the closest terminal is Washington Dulles International Airport (IAD). It's about 40 miles (64 kilometers) to the southeast from the main area. Choose an in-flight film, settle in and you'll be landing in no time.

Frequently asked questions

How much are vacation packages to Shepherdstown?
CA $845 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 88 kilometers from Shepherdstown.
Which airport is best for Shepherdstown?
Ronald Reagan Washington National Airport (DCA) (88 kilometers away from downtown), Washington Dulles Intl. Airport (IAD) (64 kilometers away from central Shepherdstown) and Hagerstown Regional Airport (HGR) (31 kilometers 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.

Photos of local treasures

Browse Shepherdstown vacation photos for more inspiration

A street lined with brick buildings, including a bank and a restaurant.
A historic street with red brick buildings, a church steeple, and a sign for a local shop.
A street with a red brick building, a sign for Maria's Taco, and a sign for Grapes & Grains Gourmet.
A row of bicycles parked against a metal bike rack on a city street.
A vintage storefront with a sign reading "Open Soon... Pop on in!" and a vintage suitcase.