Book Exclusive Shepherdstown Vacation Packages

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Shepherdstown flight + hotel packages

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Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Northwest
Price was CA $748, price is now CA $555 per person
CA $555
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Stay at this aparthotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and Arlington National Cemetery are located nearby.
The Georgetown Inn

The Georgetown Inn

4.5 out of 5
Northwest
Price was CA $932, price is now CA $657 per person
CA $657
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Arlington National Cemetery are located nearby.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was CA $989, price is now CA $720 per person
CA $720
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions National Mall and Capital One Arena are located nearby.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was CA $868, price is now CA $651 per person
CA $651
per person
Nov 25 - Nov 28
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the bar in our reviews. Popular attractions White House and Capital One Arena are located nearby.
The Georgetown House

The Georgetown House

3 out of 5
Northwest
Save 100% on your flight
Price was CA $2,095, price is now CA $1,603 per person
CA $1,603
per person
Oct 19 - Oct 26
found 13 hours ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
Stay at this hotel in Washington. Enjoy free WiFi, room service, and premium TV channels. Popular attractions White House and Arlington National Cemetery 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 $138 per night
CA $138
CA $154 total
Oct 18 - Oct 19
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 $58 per night
CA $58
CA $149 total
Oct 1 - Oct 2
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
Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

2.5 out of 5
25 Union St Harpers Ferry WV
Free cancellation
The price is CA $146 per night
CA $146
CA $163 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this business-friendly hotel in Harpers Ferry. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races are located nearby.
Breakfast included
Parking included
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 $131 per night
CA $131
CA $146 total
Oct 8 - Oct 9
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
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

3 out of 5
89 ALL STAR COURT Hagerstown MD
Free cancellation
Reserve now, pay when you stay
The price is CA $142 per night
CA $142
CA $159 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this business-friendly hotel in Hagerstown. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hagerstown Field House and Hagerstown Premium Outlets are located nearby.
Pool
Breakfast included
Comfort Inn Frederick - Ballenger Creek

Comfort Inn Frederick - Ballenger Creek

2.5 out of 5
7300 Executive Way Frederick MD
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $137 total
Oct 18 - Oct 19
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 helpful staff and the clean rooms in our reviews. Popular attractions Regal Westview and Westview Promenade are located nearby.
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

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 $555 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.