Search Villas 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 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 7 Villas in Shepherdstown with updated reviews, rates, and availability.

Beautiful Mansion in the Country & Wedding Venue
Outdoor dining

Beautiful Mansion in the Country & Wedding Venue

9.8 out of 10, Exceptional, (9)
"The stay and place was awesome and my family and I will definitely be booking again "
The price is SAR 5,813
SAR 11,026 total
includes taxes & fees
17 Feb - 18 Feb
Beautiful Mansion in the Country & Wedding Venue
Stunning Former Winery w/ Pool & Mtn Views!
Berryville Vacation Rental | 8BR | 5.5BA | Stairs Required | 7,078 Sq Ft

Stunning Former Winery w/ Pool & Mtn Views!

9.4 out of 10, Exceptional, (9)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
Stunning Former Winery w/ Pool & Mtn Views!
Private10000sf Retreat GuitarPool Hottub-Wine Area

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (21)
"Thank you for making our stay so seamless. We were comfortable and able to have a lot of fun and get a lot accomplished. It’s a great area!"
The price is SAR 4,677
SAR 8,410 total
includes taxes & fees
3 Mar - 4 Mar
Private10000sf Retreat GuitarPool Hottub-Wine Area
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Exterior

Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen

9.2 out of 10, Wonderful, (35)
"Nice creek view from the kitchen and family room. Very quite and cozy place to relax. (It is recommended not over 4 people.) It might be good if you visit here for canoeing.Still it has room for improvement. Mattresses are not in good shape. Floors are squeaking all over. (If you wake up in the middle of the night and gotta go, then, all other families will hear your foot steps.)"
Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Interior

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (5)
"This home was spectacular inside and outside! The decor was amazing! This home provided for a wonderful time had by all. Very impressive and well thought out floor plan gave us plenty of room to sit and eat, watch tv, play games and even slip away for a nap! The inside of this home had everything our family needed to enjoy Thanksgiving, just fantastic! The outside was just as special! We took walks with the kids around the quarry - stunning - the fire pit provided for many hours of outside...
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Stunning Former Winery w/ Pool & Mtn Views!
Exterior

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
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 SAR 165
SAR 411 total
includes taxes & fees
3 Mar - 4 Mar
❤️ 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

Why book your villa in Shepherdstown with Expedia?
With Expedia, it’s easy to find your dream villa in Shepherdstown. Traveling with the kids? Make the most of our helpful filters to look for stays with a pool or free WiFi. If you have a budget in mind, choose how much you’re willing to spend and the star rating of the property. We’ll help you find the perfect stay that suits your taste and style.
How can I find cheap villas in Shepherdstown?
An excellent way to compare cheap villas in Shepherdstown is with Expedia’s useful filter tool. Refine your search results by star rating, budget and amenities to find awesome bargains in only a few keystrokes.