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

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Check availability on Shepherdstown Romantic Hotels

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 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.
A circular fire pit surrounded by grass and small plants, with a bench and logs nearby.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
United States
Dennis C.
AED 169
AED 411 total
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A room with large windows, wooden floors, and a ceiling fan.
A wooden deck leading to a cabin surrounded by dense forest.
A wooden deck with a table and benches, surrounded by a railing, and a glass door leading to a lush green garden.
A wooden cabin surrounded by snow-covered trees.

2. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
United States
Erinn
AED 735
AED 1,207 total
includes taxes & fees
7 Oct - 8 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.
A rustic cabin interior with a wooden ceiling, a leather sofa with patriotic pillows, a wooden coffee table, and a television on a wooden dresser.
A rustic log cabin with a metal roof, a porch with outdoor seating, and a star decoration on the front.
A rustic cabin with a porch, wooden rocking chairs, a table with potted plants, and a mailbox.

3. 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
United States
Cindy B.
AED 533
AED 1,040 total
includes taxes & fees
26 Oct - 27 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A stone wall adjacent to a water feature with a wooden structure and pipes.
A rustic room with stone walls, a round table with metal chairs, a window with natural light, and a wooden beam ceiling.
A stone house with a balcony and a porch, surrounded by greenery.
A cozy living room with a fireplace, a ceiling fan, and a blue armchair.

4. UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803

UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
Hagerstown
United States
WAYNE M.
AED 426
AED 658 total
includes taxes & fees
13 Oct - 14 Oct
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
A playground with swings, a slide, and a fire pit area with chairs.
A cozy cabin-style kitchen with wooden cabinets, a granite countertop, and a dining table with red chairs.
A cabin with a metal roof, surrounded by trees, and two blue chairs in front.
A cabin interior with wooden walls, a sofa, two beds, a ladder, and a small table.

5. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
United States
Image M.
AED 981
AED 1,807 total
includes taxes & fees
7 Oct - 8 Oct
Glamping Clear Spring Maryland 3-Cabin Campground
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.
A bedroom with a bed, dresser, mirror, and bedside table.
A backyard patio with a table and chairs, surrounded by a wooden fence and various plants.
A cozy living room with a sofa, a patterned rug, and a large window with curtains.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
United States
Jennifer W.
AED 514
AED 1,145 total
includes taxes & fees
1 Nov - 2 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A spacious living room with a large wooden dining table, a fireplace, and large windows offering a view of the outdoors.
A cabin with a deck, surrounded by trees, and a fire pit with chairs.
A modern kitchen with stainless steel appliances, white cabinetry, and a granite countertop.
A modern living room with a fireplace, a sofa, a coffee table, and a bookshelf.

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

Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
The Woods
United States
Scott F.
AED 640
AED 1,455 total
includes taxes & fees
8 Oct - 9 Oct
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
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Top Shepherdstown Hotel Reviews

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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