Title: Book the Best ROMANTIC Hotels in Shepherdstown, WV from CA $147 - Shepherdstown Romantic Getaways | 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)[Shepherdstown Vacation Packages](https://expedia.ca/Shepherdstown.d56114.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135495-Shepherdstown.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in Shepherdstown, WV from CA $147 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Shepherdstown Romantic Hotels Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=56114&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=56114&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=56114&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=56114&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Shepherdstown Romantic Hotels ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/9c1d9621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/0f0c1ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/80506691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34830000/34821800/34821722/1a9ef301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️ Secluded 1940s Romantic Tiny House on the River Shepherdstown 10/10 Exceptional (63) "My second say at this cabin, definitely want to visit again. The cabin is private, clean and cozy perfect base of operations for day trips around the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline D. CA $55 CA $147 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Martinsburg-Hotels-Secluded-1940s-Romantic-Tiny-House-On-The-River.h34821722.Hotel-Information) ![1 bedroom, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/164a5d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/a3d383f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester Winchester 9.4/10 Exceptional (753) "Nice place, very quiet, comfie beds, and great staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $156 CA $169 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/58000000/57940000/57930500/57930476/4319937e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, foosball, books](https://images.trvl-media.com/lodging/58000000/57940000/57930500/57930476/059eea15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57940000/57930500/57930476/18b383ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/58000000/57940000/57930500/57930476/050e4f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Pine Tree Nest Frederick 9.4/10 Exceptional (11) "Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David S. CA $112 CA $237 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Frederick-Hotels-Cozy-Pine-Tree-Nest.h57930476.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/f92e85d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 King Bed Corner Room w/ Sofabed Nonsmoking](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/80cf47d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/9047f16d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21500/21470/e9944ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Frederick Frederick 8.2/10 Very good (1001) "Decent stay..very convenient to highway and eating options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $139 CA $154 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Frederick-Hotels-Hampton-Inn-Frederick.h21470.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/eaa4b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Bamford Suite)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/50b1e67b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/46449a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/f8c19c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn Charles Town 8.6/10 Excellent (670) "We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nataliya CA $233 CA $296 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/55851da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/aef6bd38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/53e738c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33420000/33415400/33415316/286a3bf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803 Hagerstown 10/10 Exceptional (122) "We were very pleased with our stay. We enjoyed the privacy and the house" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine B. CA $144 CA $230 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Hagerstown-Hotels-Springhouse-1803-Unique-Historic-Home.h33415316.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66710000/66702200/66702131/85d51081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66710000/66702200/66702131/ac07479b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/67000000/66710000/66702200/66702131/009d300e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66710000/66702200/66702131/acc9da32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antietam Toll House~ an historic waterfront cabin with fully fenced yard. Waynesboro 9.8/10 Exceptional (86) "Everything worked as expected, good experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John R. CA $126 CA $311 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Waynesboro-Hotels-Antietam-Toll-House-An-Historic-Waterfront-Cabin-With-Fully-Fenced-Yard.h66702131.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/538bb833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/24e9ba52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/72598aee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36390000/36380300/36380283/3a88e4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location. Middletown 9.6/10 Exceptional (104) "Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nino CA $98 CA $261 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Frederick-Hotels-Vintage-Cabin-In-The-Of-Middletown.h36380283.Hotel-Information) ![](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/0ed0ba48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/7d8e3efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/7c41d2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21300000/21298100/21298018/afee337d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT. Downtown Frederick 9.4/10 Exceptional (117) "We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie C. CA $170 CA $404 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Frederick-Hotels-RETREAT-On-The-CREEK-Businees-Travelor-Or-Weekend-Getaway-HISTORIC-DISTRICT.h21298018.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6a9fc093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (504) "Great place to stay to go to the casino" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $164 CA $198 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15®ionId=56114&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Shepherdstown ### Shepherdstown attractions for couples Nestled along the banks of the Potomac River, Shepherdstown, West Virginia, is rich in history and natural beauty, making it a charming choice for quality-seeking travellers. Begin your adventure with a visit to the historic Shepherdstown Museum, where you can delve into the town's rich Civil War history and explore fascinating exhibits. Outdoor enthusiasts will love the nearby C&O Canal National Historical Park, offering scenic hiking and biking trails that wind alongside the river, perfect for a family day out. Don’t miss a stroll through the picturesque streets lined with unique shops and art galleries, particularly the contemporary works at the Shepherdstown Art Gallery. For a more relaxed experience, enjoy a leisurely afternoon at the Rumsey Monument, which offers stunning views of the surrounding countryside. After a day of exploration, unwind at one of the charming local inns, such as the Thomas Shepherd Inn, where you can indulge in personalised service and enjoy complimentary breakfast featuring local ingredients. The quaint atmosphere of Shepherdstown enhances your stay, providing a perfect base to create lasting memories with your loved ones. ## Top Shepherdstown Hotel Reviews ![Hampton Inn & Suites Charles Town](//images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed_y.jpg) ### Hampton Inn & Suites Charles Town 10/10 Excellent "Smooth check in. Comfortable. Good waffles." [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) ![Country Inn & Suites by Radisson, Hagerstown, MD](//images.trvl-media.com/lodging/2000000/1220000/1216300/1216228/31529ad2_y.jpg) ### Country Inn & Suites by Radisson, Hagerstown, MD 10/10 Excellent "Room was very clean and the bed and pillows were very comfortable!!!" [](https://expedia.ca/Hagerstown-Hotels-Country-Inn-Suites-By-Radisson.h1216228.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Shepherdstown? > If you and your partner need a romantic escape, we've got just the ticket. Our guests also enjoy Shepherdstown for its riverfront and historic landmarks. If you'd like to explore some of the area's notable sights, you might make a stop by Shepherdstown Opera House, Shepherdstown Museum, or Shepherdstown Historic District. If you're interested in staying close to a certain attraction, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list. ### When is the best time of year for a romantic getaway to Shepherdstown? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Shepherdstown: The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Shepherdstown is 47 inches. ### What is there to do in Shepherdstown? > There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Shepherdstown. Couples looking to get out in nature will enjoy Shepherdstown for its riverfront. Shepherdstown Opera House, Shepherdstown Museum, and Shepherdstown Historic District are worth a stop when you're out and about. ### What's the best way to get to Shepherdstown and around town during my romantic getaway? > These transportation options in Shepherdstown might help your romantic trip get off to a smooth start: Make your way to Shepherdstown with a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional), which is the closest major airport located 10.1 mi (16.3 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Harpers Ferry](https://www.expedia.ca/4Star-Harpers-Ferry-Hotels.s40-0-d7561.Travel-Guide-Filter-Hotels) - [Aparthotels in Bedington](https://www.expedia.ca/Bedington-Apart-Hotels.d553248635975875967-aaApartHotels.Travel-Guide-Accommodation) - [Cabin Rentals in Bedington](https://www.expedia.ca/Bedington-Cabins.d553248635975875967-aaCabins.Travel-Guide-Accommodation) - [Bedington Hotels](https://www.expedia.ca/Bedington-Hotels.d553248635975875967.Travel-Guide-Hotels) - [Lodges in Bedington](https://www.expedia.ca/Bedington-Lodges.d553248635975875967-aaLodges.Travel-Guide-Accommodation) - [Resorts in Bedington](https://www.expedia.ca/Bedington-Resort-Hotels.d553248635975875967-aaResortHotels.Travel-Guide-Accommodation) - [Resorts in Berkeley](https://www.expedia.ca/Berkeley-Resort-Hotels.d553248635975849730-aaResortHotels.Travel-Guide-Accommodation) - 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