A street lined with brick buildings, including a bank and a restaurant.

Shepherdstown Vacations from $330

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The Latest Shepherdstown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 3 - Sep 7

    Kellogg Conference Hotel at Gallaudet University + Flight

    Northeast
    4 nights
    3.0 star property
    8.2/10 - Very Good (1,000 reviews)
    "The stay wasn’t great at all. We had very noisy neighbours. When we called the reception the first time, they said they would take care of it, but no one did. We called the second time, then someone came and knocked on our door first to confirm that it was us that called, which is unprofessional. It sounded like he talked to the noisy neighbours. Nothing changed. We had just enough after and had to bang on the wall and yell for the neighbours to stop. After that, they were quiet. After we got..."
    Reviewed July 13, 2026
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - BWINonstop BWI - ATLNonstop
    Save 100% on your flight
    $528
    $330
    per traveler
    found 1 day ago
    Kellogg Conference Hotel at Gallaudet University
  • Oct 2 - Oct 5

    Hotel Burg + Flight

    Leesburg's Old and Historic District
    3 nights
    4.0 star property
    9.6/10 - Exceptional (95 reviews)
    "Amazing experience"
    Reviewed July 12, 2026
    Roundtrip Boston (BOS) - Baltimore (BWI)
    BOS - BWINonstop BWI - BOSNonstop
    Save 100% on your flight
    $1,674
    $1,005
    per traveler
    found 5 hours ago
    Hotel Burg
  • Oct 4 - Oct 10

    The River Inn + Flight

    Northwest
    6 nights
    4.0 star property
    9.4/10 - Exceptional (2,031 reviews)
    "Clean and specious rooms. Perfect for my family of 5."
    Reviewed July 18, 2026
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - DCANonstop DCA - ATLNonstop
    Save 100% on your flight
    $1,142
    $713
    per traveler
    found 1 day ago
    The River Inn
  • Oct 4 - Oct 10

    Phoenix Park Hotel + Flight

    Northwest
    6 nights
    3.5 star property
    9.4/10 - Exceptional (2,181 reviews)
    "Good"
    Reviewed July 18, 2026
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - DCANonstop DCA - ATLNonstop
    Save 100% on your flight
    $1,165
    $730
    per traveler
    found 1 day ago
    Phoenix Park Hotel
  • Oct 4 - Oct 10

    Hotel Washington + Flight

    Downtown Washington D.C.
    6 nights
    5.0 star property
    9.0/10 - Wonderful (2,440 reviews)
    "Beautiful, fantastic location definitely would stay there again!"
    Reviewed July 17, 2026
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - DCANonstop DCA - ATLNonstop
    Save 100% on your flight
    $1,636
    $1,038
    per traveler
    found 1 day ago
    Hotel Washington

Discover the most popular places to visit in Shepherdstown

What to do in Shepherdstown

Shepherdstown Hotel Deals

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.

Frequently Asked Questions

How much does a Shepherdstown vacation package cost?

You'll find cheap prices from $330 on Expedia for your Shepherdstown getaway. 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?

If you'd like to score a cheap Shepherdstown vacation package, consider traveling in November, December and January. You'll usually find lower rates on airfares and hotels during these months — ideal for travelers wishing to save money.

How many days is enough for Shepherdstown?

Generally, a handful of days is enough to tick off the major attractions during your Shepherdstown vacation. However, if you prefer to have some time to chill out or take day tours, consider extending your itinerary.

Is it worth booking a vacation package to Shepherdstown?

Shepherdstown offers everything you need for a wonderful trip. Begin your Shepherdstown vacation on a high note by visiting top attractions like Shepherdstown Visitors Center.

How to find the best Shepherdstown package deals?

Begin your search for a Shepherdstown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shepherdstown package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Shepherdstown escape off to a flying start.

Is it cheaper to book a Shepherdstown vacation as a package?

Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Shepherdstown vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Shepherdstown?

Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Shepherdstown break.

Does Expedia offer Book Now, Pay Later Shepherdstown vacation packages?

Set off on your perfect trip to Shepherdstown with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.