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

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Check availability on Shepherdstown Historic Hotels

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

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 AED 152
AED 392 total
includes taxes & fees
8 Nov - 9 Nov
❤️ 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 AED 826
AED 1,320 total
includes taxes & fees
1 Nov - 2 Nov
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)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
The price is AED 331
AED 837 total
includes taxes & fees
1 Nov - 2 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A stone house with a balcony and a porch, surrounded by greenery.

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 AED 413
AED 644 total
includes taxes & fees
2 Nov - 3 Nov
UNIQUE HISTORIC COTTAGE - SPRINGHOUSE 1803
A rural road with a grassy area and a yellow flowering bush.

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 AED 382
AED 1,050 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 981
AED 1,807 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 367
AED 966 total
includes taxes & fees
1 Nov - 2 Nov
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.
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Top Shepherdstown Hotel Reviews

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"The room was very comfortable and the members of the personnel were very accommodating. Would stay there again should I return to Frederick. Thank you"
Louise 3-night trip
Posted 1 hour 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.