Title: Shepherdstown Vacation Packages 2026 from $866 | Expedia.com [Shepherdstown Travel Guide](https://expedia.com/Shepherdstown.dx56114)[Hotels in Shepherdstown](https://expedia.com/Shepherdstown-Hotels.d56114.Travel-Guide-Hotels)[Vacation Rentals in Shepherdstown](https://expedia.com/Shepherdstown-Vacation-Rentals.d56114.Travel-Guide-VacationRentals)[Flights to Shepherdstown](https://expedia.com/Cheap-Flights-To-Shepherdstown.d56114.Travel-Guide-Flights)[Car Rentals in Shepherdstown](https://expedia.com/Car-Rentals-In-Shepherdstown.d56114.Car-Rental-Guide) ![](https://images.trvl-media.com/place/56114/00cd2069-de0c-470a-86cc-7eb498d4fe40.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Shepherdstown Vacations from $866 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Antietam-National-Battlefield-Sharpsburg.d6091709.Vacation-Attraction), [Shepherd University](https://www.expedia.com/Shepherd-University-Shepherdstown.d553248621558642403.Vacation-Attraction) and [Antietam National Cemetery](https://www.expedia.com/Antietam-National-Cemetery-Sharpsburg.d553248621532662484.Vacation-Attraction). Whatever your travel plans or the size of your budget, organizing a tailored Shepherdstown vacation is a breeze with Expedia. ## The Latest Shepherdstown vacation packages Price found within the past 48 hours. Click for updated prices. ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/89cd8abe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Baltimore Fells Point Save 100% on your flight $866 per person Jun 7 - Jun 10 found 12 hours ago Roundtrip flight included Atlanta (ATL) to Baltimore (BWI) 9.4/10 Exceptional! (1,001 reviews) One of best hotels I’ve stayed in. Staff, the rooms, and hotel bars are top notch! Reviewed on Mar 11, 2026 ![Rosewood Washington, D.C.](https://images.trvl-media.com/lodging/6000000/5490000/5487000/5486908/c0d38507_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rosewood Washington, D.C. Northwest Save 100% on your flight $2,615 per person May 31 - Jun 7 found 14 hours ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9.2/10 Wonderful! (201 reviews) My stay at the Rosewood Hotel was absolutely wonderful from start to finish. The level of service, attention to detail, and overall atmosphere made it a truly memorable experience. From the moment I arrived, the staff was warm, welcoming, and genuinely attentive. Check‑in was smooth and effortless, and I immediately felt like a valued guest. The room was beautifully designed—spacious, spotless, and thoughtfully arranged with luxurious touches throughout. The bed was incredibly comfortable, and the overall ambiance made it easy to relax. The hotel’s amenities were equally impressive. Whether enjoying the dining options, unwinding in the lounge areas, or simply taking in the elegant décor, everything felt refined and well-curated. Every interaction with the staff felt sincere, and the service consistently exceeded my expectations. Overall, my stay at the Rosewood was exceptional. I would highly recommend this hotel to anyone looking for comfort, luxury, and top‑tier hospitality. I’m already looking forward to returning! Reviewed on Feb 19, 2026 ![Arlo Washington DC](https://images.trvl-media.com/lodging/107000000/106090000/106087200/106087178/8cf67881_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Washington DC Northwest Save 100% on your flight $989 per person Jun 13 - Jun 19 found 23 hours ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9.4/10 Exceptional! (1,340 reviews) Loved this hotel! I would definitely stay here again. The only complaint I have, is the lighting in the room. The light over the headboard wasn’t too bright. Overall, I enjoyed my stay. The hotel was nice and spotless, the staff were very friendly. Not to mention, it is close to Union Station. Reviewed on Mar 22, 2026 ![Riggs Washington DC](https://images.trvl-media.com/lodging/38000000/37200000/37192100/37192042/5bbd818e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Riggs Washington DC Downtown Washington D.C. Save 100% on your flight $1,285 per person May 31 - Jun 7 found 14 hours ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9.4/10 Exceptional! (1,427 reviews) Exceeded expectations!! Reviewed on Mar 17, 2026 ![Hilton Washington DC Capitol Hill](https://images.trvl-media.com/lodging/1000000/20000/11300/11216/e04fecb3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Washington DC Capitol Hill Northwest Save 100% on your flight $1,015 per person Jun 13 - Jun 19 found 23 hours ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9/10 Wonderful! (1,027 reviews) I had an excellent overnight stay. The door man and front desk staff were friendly, the check in process was easy, the hotel is clean and well maintained and the room was very clean and comfortable. The shower felt amazing! The food and bartenders were great for both lunch and dinner. I had to leave the evening bartenders a nice tip because they were super friendly and engaging to me as someone traveling alone for a conference in another hotel. I accidentally left my toothbrush home (go figure!) and they gave me a complimentary one, toothpaste and extra water. I was well cared for and would recommend this hotel to everyone! Reviewed on Mar 22, 2026 Don't see what you're looking for? See all available trips from Columbus to Shepherdstown [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-23/2026-04-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FDK&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Shepherdstown #### Shepherd University Explore the campus of Shepherd University, during your travels in Shepherdstown. Amble around the area's riverfront, or seek out its horseback riding. [](https://expedia.com/Shepherd-University-Shepherdstown.d553248621558642403.Vacation-Attraction) #### Shepherdstown Visitors Center 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. [](https://expedia.com/Shepherdstown-Visitors-Center-Shepherdstown.d553248621561196354.Vacation-Attraction) #### 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. [](https://expedia.com/Morgans-Grove-Park-Shepherdstown.d553248621561196357.Vacation-Attraction) ### What to do in Shepherdstown ![South Mountain Private Battlefield Tour](https://mediaim.expedia.com/localexpert/49951025/4fd142ab-eb6f-46de-991d-fb60cd1721e5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### South Mountain Private Battlefield Tour $120 per traveler [](https://expedia.com/things-to-do/south-mountain-private-battlefield-tour.a49951025.activity-details) [See all activities in Shepherdstown](https://expedia.com/things-to-do/search?rid=56114) ## Shepherdstown Hotel Deals ![Quality Inn Shepherdstown](https://images.trvl-media.com/lodging/1000000/480000/474700/474628/35bb7cb1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Shepherdstown 70 Maddex Square Dr Shepherdstown WV Fully refundable $78 nightly $88 total Apr 2 - Apr 3 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=474628&PinnedHotelID=474628&HadPinnedHotel=true®ionId=56114) ![❤️ Secluded 1940s Romantic Tiny House on the River](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown WV $120 nightly $133 total Mar 30 - Mar 31 Total with taxes and fees 9.8/10 Exceptional! (72 reviews) This was the perfect Valentine's getaway weekend for us. I booked the stay as a surprise, and my partner loved it. We are already talking about coming back some time. It was tidy, intimate, and peaceful. We cooked over the fire the first night, then on the grill the next night because it was raining. ... Reviewed on Feb 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=34821722&PinnedHotelID=34821722&HadPinnedHotel=true®ionId=56114) ![Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub](https://images.trvl-media.com/lodging/117000000/116920000/116917400/116917357/85c3966c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [See all 937 properties in Shepherdstown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F24%2F2026&endDate=3%2F25%2F2026®ionId=56114) 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. ## Find the Best Shepherdstown Vacation Packages ## Shepherdstown Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Hagerstown Regional Airport (HGR) | | Population | 2,100 | | Max Temp Winter | 40ºF | | Max Temp Summer | 85ºF | | Top Sights | [Bolivar Heights Scenic Overlook](https://www.expedia.com/Bolivar-Heights-Scenic-Overlook-Harpers-Ferry.d553248633963503100.Vacation-Attraction), [Shepherdstown Museum](https://www.expedia.com/Shepherdstown-Museum-Shepherdstown.d553248621532662479.Vacation-Attraction) and [John Browns Fort](https://www.expedia.com/John-Browns-Fort-Harpers-Ferry.d553248633961488742.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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