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

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Check availability on Shepherdstown Romantic Hotels

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

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 1,328 total
includes taxes & fees
25 Nov - 26 Nov
Antietam Creek - Quiet 2 Bedroom Cabin
A hammock on a grassy area with a view of a river and forested hills.

3. La Soledad Lavender Farm on the Potomac

La Soledad Lavender Farm on the Potomac
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Terrific place and very friendly and accommodating host"
United States
Michel R.
The price is AED 1,102
AED 1,572 total
includes taxes & fees
26 Nov - 27 Nov
La Soledad Lavender Farm on the Potomac
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

4. 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 367
AED 837 total
includes taxes & fees
30 Oct - 31 Oct
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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 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 stone wall adjacent to a water feature with a wooden structure and pipes.

6. 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 playground with swings, a slide, and a fire pit area with chairs.

7. 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
29 Oct - 30 Oct
Glamping Clear Spring Maryland 3-Cabin Campground
A spacious living room with a large wooden dining table, a fireplace, and large windows offering a view of the outdoors.

8. 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, (64 reviews)
"As expected. Very nicely appointed for a cabin in the woods. Did not use the pool or other amenities but they looked nice."
United States
Scott F.
The price is AED 654
AED 1,536 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Pet-Friendly w Fire Pit, Wifi & Pool Access
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

9. 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

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

10/10 Excellent
"Great staff always a good stay here!!!"
Michele 2-night trip
Posted 23 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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