Title: Shepherdstown Vacation Packages & Trips 2026 from CA $731 | 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. ![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 CA $731 per person Jun 12 - Jun 15 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) 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 ![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 $761 per person Jun 12 - Jun 15 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) 8.6/10 Excellent! (1,008 reviews) Cleaning staff amazing Reviewed on Mar 20, 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 $949 per person Jun 12 - Jun 15 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) 9.4/10 Exceptional! (1,065 reviews) This is where you stay when you want a piece of mind! Specialized professionals dedicated towards the customer's experience! Reviewed on Mar 22, 2026 ![Kellogg Conference Hotel at Gallaudet University](https://images.trvl-media.com/lodging/1000000/560000/552000/551972/a151aab7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kellogg Conference Hotel at Gallaudet University Northeast CA $810 per person Jun 12 - Jun 15 found 2 hours ago Roundtrip non-stop flight included Toronto (YTO) to Washington (DCA) 8.2/10 Very Good! (1,001 reviews) Clean room. Kind staff. Food options available Reviewed on Mar 22, 2026 ![Placemakr Buzzard Point](https://images.trvl-media.com/lodging/114000000/113170000/113163000/113162985/4d19de4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Buzzard Point Southwest CA $1,129 per person May 8 - May 11 found 12 hours ago Roundtrip flight included Montreal (YUL) to Washington (DCA) 9.2/10 Wonderful! (157 reviews) I loved my stay there. The staff was so nice and helpful. I would definitely stay again. Reviewed on Mar 5, 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 $107 CA $120 total Apr 2 - Apr 3 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%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 $89 CA $183 total Apr 6 - Apr 7 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=06%2F04%2F2026&endDate=07%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=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=116917357&PinnedHotelID=116917357&HadPinnedHotel=true®ionId=56114) [See all 939 properties in Shepherdstown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%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