Search Resorts in Shepherdstown

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 2 Resorts in Shepherdstown with updated reviews, rates, and availability.

GolfView Chalet at the Woods Resort, Central Air and Heat
Living area

GolfView Chalet at the Woods Resort, Central Air and Heat

9.8 out of 10, Exceptional, (7)
"In general a very nice place. Needs some small touches. The fire place was not cleaned. Need instructions on how to open windows. Kitchen not fully equipped: One wine glass No dish towels or drainage rake or cloth for drying dishes or even for air drying No measuring cup No salad bowl No apron Window in kitchen table area fell one two times Toilet tissue holder in second bathroom kept falling "
GolfView Chalet at the Woods Resort, Central Air and Heat
The Lake Escape Townhouse @ The Woods Resort
Outdoor dining

The Lake Escape Townhouse @ The Woods Resort

The Lake Escape Townhouse @ The Woods Resort
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.
Don't see what you're looking for?
See all available properties in Shepherdstown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is AED 162
AED 403 total
includes taxes & fees
24 Feb - 25 Feb
❤️ Secluded 1940s Romantic Tiny House on the River
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (17)
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful and cozy. Owners were super responsive when needed and very easy to work with. Would definitely go back in nicer weather! "
Charming Cabin in the Woods with River Access
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
Welcome To Graycliff Hall. Your beautiful riverside estate.

Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub

8.0 out of 10, Very Good, (1)
"Our family had an unforgettable New Year's holiday at this incredible rental property! From the moment we arrived, we were amazed by the beautiful house, its spaciousness, and the plethora of facilities available to accommodate everyone in our group. The property was clean, well-organized, and tastefully decorated, making it a warm and inviting space for our celebration.The true gem of our stay was the exceptional hospitality provided by the property's management, especially the remarkable Miss...
Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub
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.

Frequently asked questions

What can I expect from a resort vacation in Shepherdstown?
You deserve some time off, and a resort is the ideal place to indulge in all the services and amenities you need for a relaxing trip to Shepherdstown. One of the comfortable resorts in the surrounding area could be just what you’re searching for, whether you’re hoping for a luxurious suite, shopping possibilities, or activities for the kids.
What's the best resort for my stay in Shepherdstown?
Our highest-rated resorts around Shepherdstown: GolfView Chalet at the Woods Resort, Central Air and Heat - Family-friendly resort. 18.1 mi (29.2 km) from Shepherdstown. Features a hot tub. The Lake Escape Townhouse @ The Woods Resort - Family-friendly resort. 17.6 mi (28.3 km) from Shepherdstown. Has a water park, a sauna, and a fitness center.
What can I do in Shepherdstown?
Learn about the local history at monuments like Rumsey Monument, or discover the shopping possibilities at Maddex Square. Additional attractions in the area include Shepherdstown Visitors Center and Shepherdstown Opera House.
What's the weather like 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's the best way to get to and around Shepherdstown?
Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 10.1 mi (16.3 km) from the city center. You can also search for flights into Hagerstown, MD (HGR-Hagerstown Regional), which is 19.4 mi (31.2 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.