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

Find Historic 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 Historic Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Shepherdstown historic hotels

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is ￥6,541
￥16,867 total
includes taxes & fees
Nov 8 - Nov 9
❤️ Secluded 1940s Romantic Tiny House on the River
A room with large windows, wooden floors, and a ceiling fan.

2. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is ￥35,435
￥57,093 total
includes taxes & fees
Nov 11 - Nov 12
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.

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
9.6 out of 10, Exceptional, (117 reviews)
"We had a wonderful stay at the cabin. Everything looked exactly like the photos and the atmosphere was quaint, calm and relaxing. We were conveniently located to several restaurants and the area was lovely. Overall, we were very happy with our experience."
United States
Lyssa C.
The price is ￥14,219
￥36,006 total
includes taxes & fees
Nov 1 - Nov 2
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.

4. UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803

UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
Hagerstown
10.0 out of 10, Exceptional, (139 reviews)
"GREAT TIME WILL STAY AGAIN"
United States
WAYNE M.
The price is ￥17,774
￥27,680 total
includes taxes & fees
Nov 2 - Nov 3
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
A lakeside setting with wooden chairs and a picnic table, surrounded by lush greenery and trees.

5. 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, (110 reviews)
"This was our 4th stay and enjoyed every one!"
United States
Anonymous traveler
The price is ￥16,431
￥45,184 total
includes taxes & fees
Nov 2 - Nov 3
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
A playground with swings, a slide, and a fire pit area with chairs.

6. Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Welcoming and spacious for all invitees and we did not even have a chance to explore all the areas that were surrounding as it was a work related trip but will get out there at some later point for a completely relaxing stay for sure"
United States
Image M.
The price is ￥42,191
￥77,745 total
includes taxes & fees
Oct 29 - Oct 30
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.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (146 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is ￥15,799
￥41,532 total
includes taxes & fees
Nov 1 - Nov 2
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"My room was amazing! modern, attractive and clean. The firmness of the bed was perfect. I slept well."
Malika 1-night trip
Posted 3 hours ago
Best Western Historic Frederick

Frequently asked questions

What should a history buff expect from a stay in Shepherdstown?
A trip to the significant historical sites in Shepherdstown is likely first on your travel itinerary. Why not appreciate the riverfront during your visit?
How many historically relevant hotels will I find in Shepherdstown?
Shepherdstown is home to 19 hotel accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Shepherdstown?
Shepherdstown is notable for landmarks like Shepherdstown Historic District. Cultural venues include Shepherdstown Opera House and Shepherdstown Museum. A couple of additional sights to add to your agenda are Shepherdstown Visitors Center and Rumsey Steamboat Museum.
What is a historic hotel like in Shepherdstown?
When you book a historic hotel, you'll stay in a place that has a national historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are typically preserved in the guestrooms or communal spaces of such hotels in Shepherdstown, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. The term "historic hotel" is more common in the U.S., while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to emphasize the physical building and architecture. A heritage hotel draws meaning mainly from the cultural value that the place has and how it inspired the surrounding community.
Do historic hotels in Shepherdstown have modern facilities?
Yes, efforts are made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Tourists who book a stay should expect the popular amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. Booking a historic hotel in Shepherdstown doesn't mean you will stay in a place that's uncomfortable for guests or rundown.

Explore a world of travel with Expedia