Search Romantic Hotels in Shepherdstown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shepherdstown Romantic Hotels

Our top choices for Shepherdstown romantic hotels

Pillow-top beds, desk, laptop workspace, blackout curtains
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (779)
"The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. "
United States
Yolanda
The price is 2.817.480 ₫
3.065.417 ₫ total
includes taxes & fees
21 Dec - 22 Dec
SpringHill Suites by Marriott Winchester
Restaurant
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
Charles Town
8.6 out of 10, Excellent, (522)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is 3.419.647 ₫
4.093.106 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Inn at Charles Town - Hollywood Casino
Property amenity
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is 4.182.813 ₫
5.342.424 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Hillbrook Inn
Restaurant
Visitation Hotel Frederick, a Tribute Portfolio Hotel

Visitation Hotel Frederick, a Tribute Portfolio Hotel

Visitation Hotel Frederick, a Tribute Portfolio Hotel
3.5 star property
Downtown Frederick
8.4 out of 10, Very good, (43)
"Very clean Room. Was surprised there was no dresser in the room. Also I stayed in the suite"
United States
James
The price is 4.945.716 ₫
5.489.745 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Visitation Hotel Frederick, a Tribute Portfolio Hotel
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

Top Shepherdstown Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Shepherdstown?
If you and your partner need a romantic holiday, 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 Historic District or Cress Creek Country Club Golf Course. If you'd like to stay close to a certain attraction, you can sort by neighbourhood or distance 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, take a look at these details about year-round temperatures in Shepherdstown: The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Shepherdstown is 1201 mm.
What is there to do in Shepherdstown?
There's nothing better than wandering around 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 Historic District and Cress Creek Country Club Golf Course 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 go off without a hitch: 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 centre. If you'd like to explore around the area, you may want to rent a car for your trip.