A street lined with brick buildings, including a bank and a restaurant.

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Check availability on Shepherdstown Romantic Hotels

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Shepherdstown romantic hotels

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.
A hammock hanging from a tree by a lake.
A room with a wooden table, two chairs, a small shelf with a pitcher and bowl, a framed picture, and a window with curtains.
A compact kitchen with white cabinets, a sink, and a countertop with various kitchen items. There is a bed with a patterned bedspread and pillows, and a window with curtains.

1. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
United States
Dennis C.
AED 152
AED 392 total
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A large house with a prominent tower, surrounded by lush greenery and a vast landscape.
A wooden staircase with a handrail leading to a door with a wreath.
A house with a green roof and white walls, a flag, and a vase with flowers in the foreground.
A room with two chairs facing a large window, a chandelier, and a table with candles.

2. Antietam Overlook Farm

Antietam Overlook Farm
Keedysville
United States
jossely
AED 714
AED 873 total
includes taxes & fees
19 Oct - 20 Oct
Antietam Overlook Farm
A staircase with a stone wall, wooden steps, and a red carpet leading to a room with a wooden table and chairs.
A red brick building with a white door, a welcome sign, and outdoor seating with metal chairs and tables.
A bedroom with a bed, curtains, a ceiling fan, a dresser, and a rustic wall.
A staircase leading to a living area with a rug, bench, and framed pictures on the wall.

3. Light Horse Inn

Light Horse Inn
Harpers Ferry
United States
Rich
AED 464
AED 496 total
includes taxes & fees
16 Nov - 17 Nov
Light Horse Inn
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.
A rustic cabin with a porch, stone foundation, and a view of the surrounding forest.
A spacious loft bedroom with a lofted sleeping area, a wooden staircase, and a large window providing natural light.
A paved road flanked by trees with green and yellow leaves, leading into a forested area.

4. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
United States
Miki M.
AED 542
AED 1,028 total
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access
A nighttime forest path lit by string lights.
A casino with slot machines, red chairs, and a colorful carpet.
A glass of red wine with a label, a fire pit, and two Adirondack chairs in a natural setting.
A dining area with a round wooden table, black chairs, a chandelier, and a view through a sliding glass door to a deck.

5. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
United States
Nancy D.
AED 544
AED 1,267 total
includes taxes & fees
27 Oct - 28 Oct
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.
A bedroom with a large bed, wooden ceiling, a window with a view of trees, a painting on the wall, and a door with a glass panel.
A spacious living room with wooden walls and large windows, a fireplace, and a view of the outdoors.
A rustic kitchen with wooden beams, stone walls, and a fireplace.

6. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
United States
Jared
AED 433
AED 1,436 total
includes taxes & fees
3 Nov - 4 Nov
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A room with large windows, wooden floors, and a ceiling fan.
A wooden deck with a table and benches, surrounded by a railing, and a glass door leading to a lush green garden.
A wooden deck leading to a cabin surrounded by dense forest.
A wooden cabin surrounded by snow-covered trees.

7. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
United States
Erinn
AED 735
AED 1,219 total
includes taxes & fees
19 Oct - 20 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A two-story house with a front porch, American flags, and a mailbox.
A bedroom with a four-poster bed, a fireplace, a television, and a large window with curtains.
A garden with a statue, flowering shrubs, and a brick pathway.
A staircase with a red carpet, a wooden chair, a table with a lamp, and a Christmas tree.

8. The Carriage Inn B&B

The Carriage Inn B&B
Charles Town
United States
Meredith
AED 619
AED 699 total
includes taxes & fees
22 Oct - 23 Oct
The Carriage Inn B&B
A bedroom with a bed, a table, and a view of the outdoors.
A green house with a door leading to a bedroom. There is a welcome mat outside the door, and a window with a curtain on the right side.
An aerial view of a cemetery surrounded by lush greenery and hills, with a bridge crossing a river in the background.
A modern bathroom with a glass-enclosed shower, a white sink with two faucets, and a mirror with a woven frame.

9. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
United States
Michael
AED 511
AED 811 total
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
A house surrounded by lush greenery and lavender fields under a clear sky with a rainbow.
A doorway leading to a stone pathway with a grassy area and trees in the background.
A modern living room with a sofa, coffee table, and TV. There is a dining area with a table and chairs. The room has a large window and a door leading outside.
An outdoor garden setting with a gazebo, string lights, and a table with a cake and candles.

10. The Bears Den at La Soledad

The Bears Den at La Soledad
Harpers Ferry
United States
Derrick D.
AED 683
AED 1,006 total
includes taxes & fees
19 Oct - 20 Oct
The Bears Den at La Soledad
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Top Shepherdstown Hotel Reviews

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

8/10 Good
"Clean, comfortable and spacious room."
Maria 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Hagerstown, MD

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 Historic District, 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 Historic District, 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.

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