Title: Shepherdstown Vacation Packages 2026 from $400 | 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 $400 ## 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. ![Hotel Indigo Baltimore Downtown by IHG](https://images.trvl-media.com/lodging/1000000/20000/11000/10902/5652f4f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo Baltimore Downtown by IHG Mount Vernon Save 100% on your flight $400 per person Apr 23 - Apr 26 found 20 hours ago Roundtrip flight included Atlanta (ATL) to Baltimore (BWI) 9.2/10 Wonderful! (1,010 reviews) Very nice property in Baltimore. We attended a concert at CFG arena with easy walking distance. Nice bar and breakfast in the hotel, with nice rooms. Definitely recommend. Reviewed on Mar 11, 2026 ![Hilton Arlington National Landing](https://images.trvl-media.com/lodging/1000000/40000/34400/34349/w3836h2557x4y3-469ee507_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Arlington National Landing Crystal City Save 100% on your flight $590 per person May 28 - Jun 2 found 5 hours ago Roundtrip flight included Boston (BOS) to Washington (DCA) 8.8/10 Excellent! (753 reviews) Hotel was fine. Shuttle bus was awful! He did not stop at the hotel pickup where I was waiting (where I was supposed to be waiting!) and I had to chase him to get in the van. Then the next day he drove right past it headed to terminal two and I had to tell him to stop that he missed the hotel shuttle drop off and I need to get off the van. So instead of circling back to the stop, which would have been simple to do, he just pulled over half way between terminal 1 and 2 and just let me out to walk back!!!! What a nightmare! Reviewed on Feb 28, 2026 ![The Watermark Hotel](https://images.trvl-media.com/lodging/71000000/70020000/70011400/70011341/6573481c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Watermark Hotel Save 100% on your flight $922 per person May 23 - May 30 found 1 day ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9.6/10 Exceptional! (2,785 reviews) My favorite spot in Tysons Reviewed on Mar 16, 2026 ![citizenM Washington DC NoMa](https://images.trvl-media.com/lodging/71000000/70980000/70972300/70972295/f681eb4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### citizenM Washington DC NoMa Northeast Save 100% on your flight $728 per person May 23 - May 30 found 1 day ago Roundtrip flight included Atlanta (ATL) to Washington (DCA) 9.2/10 Wonderful! (2,814 reviews) The room was good, modern and fun! I think the cleanliness could be better. The majority of the staff is amazing but others could use some hospitality reminders. The facilities and location were great! The buffet was good, and there is also a Starbucks around the corner! Reviewed on Mar 15, 2026 ![Kimpton Hotel Monaco Washington DC by IHG](https://images.trvl-media.com/lodging/1000000/880000/871400/871361/587350fd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Monaco Washington DC by IHG Downtown Washington D.C. Save 100% on your flight $1,127 per person Jun 8 - Jun 12 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 8.4/10 Very Good! (1,002 reviews) Everything was EXCELLENT!! The accommodation fit our need in every way. As it’s a historic building there was a “smell” that wasn’t preferred but that comes with age, I suppose (pun intended). Reviewed on Mar 14, 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/2026-04-17/2026-04-24/?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 Mar 29 - Mar 30 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%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=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [See all 938 properties in Shepherdstown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F18%2F2026&endDate=3%2F19%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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