Title: Shepherdstown Vacation Packages & Trips 2026 from CA $1,352 | Expedia.ca [Hotels in Shepherdstown](https://expedia.ca/Shepherdstown-Hotels.d56114.Travel-Guide-Hotels)[Vacation Rentals in Shepherdstown](https://expedia.ca/Shepherdstown-Vacation-Rentals.d56114.Travel-Guide-VacationRentals)[Things to do in Shepherdstown](https://expedia.ca/Things-To-Do-In-Shepherdstown.d56114.Travel-Guide-Activities)[Shepherdstown Car Rentals](https://expedia.ca/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 Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Antietam-National-Battlefield-Sharpsburg.d6091709.Vacation-Attraction), [Shepherd University](https://www.expedia.ca/Shepherd-University-Shepherdstown.d553248621558642403.Vacation-Attraction) and [Antietam National Cemetery](https://www.expedia.ca/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. ## Top Shepherdstown Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel AKA Alexandria](https://images.trvl-media.com/lodging/88000000/87420000/87417500/87417449/40ed462e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel AKA Alexandria Old Town North CA $1,352 per person May 15 - May 19 found 19 hours ago Roundtrip flight included Ottawa (YOW) to Washington (DCA) 9.6/10 Exceptional! (701 reviews) Staff was very friendly and helpful Reviewed on Mar 31, 2026 ![InterContinental Washington D.C. - The Wharf by IHG](https://images.trvl-media.com/lodging/17000000/16030000/16024200/16024166/ca057dc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Washington D.C. - The Wharf by IHG Southwest CA $1,769 per person May 15 - May 19 found 19 hours ago Roundtrip flight included Ottawa (YOW) to Washington (DCA) 9.4/10 Exceptional! (1,065 reviews) Breakfast buffet and menu food quality poor Wait staff indifferent and slow Definitely not worth $40 per person Reviewed on Apr 4, 2026 ![Washington Hilton](https://images.trvl-media.com/lodging/1000000/10000/4000/3998/67a4937a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Washington Hilton Northwest CA $1,465 per person May 14 - May 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Washington (DCA) 8.2/10 Very Good! (1,006 reviews) The room was very spacious and clean. The hotel staff was very friendly. Reviewed on Mar 28, 2026 ![Eurostars Saint Gregory Dupont Circle Georgetown](https://images.trvl-media.com/lodging/1000000/480000/470900/470863/9d56ef4f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Saint Gregory Dupont Circle Georgetown Downtown Washington D.C. CA $1,493 per person May 15 - May 18 found 14 hours ago Roundtrip flight included Toronto (YYZ) to Washington (DCA) 8.6/10 Excellent! (1,008 reviews) Wonderful staff and nice rooms Reviewed on Apr 3, 2026 ![Eaton DC](https://images.trvl-media.com/lodging/25000000/24320000/24316600/24316563/d7a96d39_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eaton DC Downtown Washington D.C. CA $1,844 per person May 15 - May 19 found 19 hours ago Roundtrip flight included Ottawa (YOW) to Washington (DCA) 9.2/10 Wonderful! (1,528 reviews) Cool hotel, very neat and friendly staff. Fun amenities such as a Record booth, speakeasy, rooftop bar. Great location to a lot of walkable spots, Reviewed on Apr 3, 2026 ## Ready to book your vacation to Shepherdstown? Choose your dates ## 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 CA $117 CA $131 total Apr 12 - Apr 13 includes taxes & fees 7.8/10 Good! (220 reviews) It's a nice inn, people are rather friendly, and the breakfast items are pretty much what you expect at a Quality Inn. The biggest issue was that the entire property is infested with ants - they are everywhere - in the room, bathroom, and dining area. The management needs to address it asap. As of ... Reviewed on Apr 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%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 CA $100 CA $197 total Apr 27 - Apr 28 includes taxes & 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.ca/Hotel-Search?startDate=27%2F04%2F2026&endDate=28%2F04%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.ca/Hotel-Search?startDate=18%2F04%2F2026&endDate=19%2F04%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [](https://expedia.ca/Hotel-Search?startDate=18%2F04%2F2026&endDate=19%2F04%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [See all 965 properties in Shepherdstown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F04%2F2026&endDate=06%2F04%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. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### 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. [](https://expedia.ca/Morgans-Grove-Park-Shepherdstown.d553248621561196357.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app