Find Romantic Hotels in Shepherdstown, WV

  • 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

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AED 238
AED 488 total
includes taxes & fees
1 Jun - 2 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is AED 275
AED 720 total
includes taxes & fees
19 May - 20 May
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Property grounds

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is AED 735
AED 1,215 total
includes taxes & fees
19 May - 20 May
Antietam Creek - Quiet 2 Bedroom Cabin

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (126 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is AED 448
AED 1,051 total
includes taxes & fees
26 May - 27 May
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Property grounds

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (100 reviews)
"Had a wonderful time!"
United States
Jesse K.
The price is AED 382
AED 884 total
includes taxes & fees
19 May - 20 May
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is AED 533
AED 642 total
includes taxes & fees
19 May - 20 May
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803

UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
Hagerstown
10.0 out of 10, Exceptional, (131 reviews)
"GREAT TIME WILL STAY AGAIN"
United States
WAYNE M.
The price is AED 413
AED 644 total
includes taxes & fees
25 May - 26 May
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
TV, foosball, books

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
The price is AED 327
AED 658 total
includes taxes & fees
18 Jun - 19 Jun
Cozy Pine Tree Nest
Dining

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
The Woods
9.8 out of 10, Exceptional, (59 reviews)
"The cabin was cozy & clean. Kitchen had all the cooking tools that was needed during my stay. It was a perfect spot for my spouse and I while visiting family in the area. "
United States
Eric S.
The price is AED 611
AED 1,476 total
includes taxes & fees
25 May - 26 May
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
Outdoor dining

Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful and beautiful place ! Access to the park could not be better. The combination of the excellent owners / host with everything else that makes up this property makes it perfect !"
United States
Christopher J.
The price is AED 881
AED 1,451 total
includes taxes & fees
19 May - 20 May
Glamping Clear Spring Maryland 3-Cabin Campground
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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Convenient location close to shopping and restaurants but off the highway so pretty quiet. Plenty of easy parking. Clean, neat, decent breakfast for a fair price. Will stay there again next year on my way through the area."
Andrew 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

Explore a world of travel with Expedia

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 Rumsey Steamboat Museum. 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 Rumsey Steamboat Museum 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.