Shepherdstown Vacation Packages
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Your Shepherdstown Vacation
When you choose a Shepherdstown vacation package, you can really enjoy your adventure to the fullest. Delve into the highlights of this fascinating city knowing that all your travel needs have been taken care of in advance. You'll want to take in the sights during your trip to Shepherdstown. Carve out some time for popular attractions like Antietam National Battlefield, Shepherd University and Antietam National Cemetery. Whatever your travel plans or the size of your budget, organizing a tailored Shepherdstown vacation is a breeze with Expedia.
Top Shepherdstown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The River Inn
Northwest
CA $1,382
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (2,084 reviews)
The staff at the front desk for check-in was absolutely friendly and professional! After a long day at DC, her warm welcome felt very refreshing. The room was very clean and comfortable. I will definitely go back.
Reviewed on Aug 24, 2026
Ready to book your vacation to Shepherdstown?
Shepherdstown Hotel Deals
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
CA $138
CA $155 total
Sep 13 - Sep 14
includes taxes & fees
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
CA $89
CA $183 total
Aug 31 - Sep 1
includes taxes & fees
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
CA $139
CA $155 total
Sep 13 - Sep 14
includes taxes & fees
8.6/10 Excellent! (1,319 reviews)
"."
Reviewed on Aug 23, 2026
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.
Shepherdstown Museum
8.0/10 (1 review)
You can browse the exhibits at Shepherdstown Museum, a museum with a story of its own, during your trip to Shepherdstown. Amble around the area's riverfront, or seek out its horseback riding.
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.
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.
Scarborough Library
Scarborough Library is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.
Shepherdstown City Hall
Shepherdstown City Hall is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.
Rumsey Steamboat Museum
2.0/10 (1 review)
You can browse the exhibits at Rumsey Steamboat Museum, a museum with a storied past, during your trip to Shepherdstown. Amble around the area's riverfront, or seek out its horseback riding.
Rumsey Monument
Find out about the history of Shepherdstown when you spend time at Rumsey Monument. Amble around the area's riverfront, or seek out its horseback riding.
Frequently asked questions
How much does a Shepherdstown vacation package cost?
You'll find cheap prices from CA $706 on Expedia for your Shepherdstown break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Shepherdstown costs.
What are the cheapest months to go to Shepherdstown?
The off-season is the best time to visit Shepherdstown if you're trying to keep costs down. Another tip for scoring cheap Shepherdstown vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Shepherdstown?
With a well-organized travel plan, you can easily visit the main Shepherdstown attractions in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your Shepherdstown vacation for longer.
Is it worth booking a vacation package to Shepherdstown?
Shepherdstown has everything you need for an unforgettable escape. Get your Shepherdstown vacation off to a flying start by visiting popular attractions like Shepherdstown Visitors Centre.
How to find the best Shepherdstown package deals?
Landing a cheap Shepherdstown package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Shepherdstown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Shepherdstown vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can tailor your Shepherdstown escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Shepherdstown?
If you have your Shepherdstown vacation dates confirmed, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Shepherdstown?
- Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Shepherdstown.
- Budget wisely: In addition to the cost of your accommodations, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Shepherdstown.
- Work out your trip length: Consider how much time you'd like to spend discovering Shepherdstown. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Shepherdstown vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
