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 Watergate Hotel
Northwest
Price was CA $1,419, price is now CA $997 per person
CA $997
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,141 reviews)
Amazing pool area, hot tub, and sauna! Honestly, it was so good that it is all I remember about the hotel and I will definitely be back! We went at Valentine's Day and they also have an amazing restaurant experience!
Reviewed on May 8, 2026
Salamander Washington DC
Southwest
Price was CA $1,982, price is now CA $1,381 per person
CA $1,381
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,089 reviews)
Rooms over rail tracks would benefit from additional sound-proofing but otherwise fantastic stay
Reviewed on May 7, 2026
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was CA $1,576, price is now CA $1,131 per person
CA $1,131
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Great staff and a he beds were very comfortable
Reviewed on Apr 21, 2026
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,542, price is now CA $1,138 per person
CA $1,138
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (1,177 reviews)
Everything was perfect, a very nice surprise.
Reviewed on May 8, 2026
The Jefferson, Washington, DC
Downtown Washington D.C.
Price was CA $2,477, price is now CA $1,868 per person
CA $1,868
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.8/10 Exceptional! (1,004 reviews)
Charming hotel and very friendly staff especially during check-in. My one and only complaint is how noisy my stay was. I highly recommend asking for a room far away from the house-keeping closet space because they are constantly in and out and shutting doors at all hours of the day. The doors to the rooms need to be sealed better but I understand it's an older hotel.
Reviewed on May 5, 2026
Shepherdstown Hotel Deals
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
The price is CA $128 per night from Jun 1 to Jun 2
CA $128
CA $143 total
Jun 1 - Jun 2
includes taxes & fees
8/10 Very Good! (231 reviews)
Room was clean and quiet. Staff were very quick and efficient. Breakfast was good. I would definitely come stay here again.
Reviewed on May 8, 2026
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown WV
The price is CA $92 per night from May 20 to May 21
CA $92
CA $186 total
May 20 - May 21
includes taxes & fees
9.8/10 Exceptional! (74 reviews)
Enjoyed my stay I appreciate the view and Rich.
Reviewed on Apr 13, 2026
Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub
Shepherdstown WV
10/10 Exceptional! (1 review)
Beautiful area!
Reviewed on Sep 1, 2025
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.
Discover the most popular places to visit in Shepherdstown
Morgan's Grove Park
Morgan's Grove Park 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, find time to visit its casinos.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
