Shepherdstown Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Shepherdstown holiday rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (77 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is HK$564
HK$1,105 total
includes taxes & fees
29 Jun - 30 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is HK$729
HK$2,779 total
includes taxes & fees
6 Jun - 7 Jun
Walk to Stores: Home in Historic Shepherdstown!
Exterior

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia
Shepherdstown
The price is HK$804
HK$1,067 total
includes taxes & fees
1 Jun - 2 Jun
"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia
Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (18 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is HK$3,252
HK$5,124 total
includes taxes & fees
28 Jun - 29 Jun
Exclusive Wooded Chalet w Magnificent River Views
Interior

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, (115 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is HK$666
HK$1,653 total
includes taxes & fees
1 Jun - 2 Jun
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (127 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is HK$776
HK$2,060 total
includes taxes & fees
1 Jun - 2 Jun
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Interior

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (11 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is HK$776
HK$1,473 total
includes taxes & fees
31 May - 1 Jun
Bring Your Own Boat - Meticulously restored house on the Potomac River
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (37 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
The price is HK$1,019
HK$3,077 total
includes taxes & fees
15 Jun - 16 Jun
Antietam Look Out - Incredible Sunset Views!
Property grounds

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, (101 reviews)
"Had a wonderful time!"
United States
Jesse K.
The price is HK$815
HK$1,895 total
includes taxes & fees
7 Jun - 8 Jun
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Terrace/patio

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (36 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is HK$830
HK$2,999 total
includes taxes & fees
10 Jun - 11 Jun
Rebels Rest - Cabin with Enchanting Sunset Views!
Smart TV

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (9 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is HK$480
HK$1,522 total
includes taxes & fees
1 Jun - 2 Jun
Pet-friendly, heart of downtown
Smart TV, fireplace

Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (37 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is HK$784
HK$3,004 total
includes taxes & fees
31 May - 1 Jun
Secluded Cabin a Stone's Throw From the A.T.!
Terrace/patio

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks

Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Sleepy Hollow
9.8 out of 10, Exceptional, (19 reviews)
"Everything was great, the property was just as the pictures showed. We had an awesome view and got lucky to see the northern lights during our stay. "
United States
Krystle W.
The price is HK$716
HK$2,272 total
includes taxes & fees
3 Jun - 4 Jun
Secluded WV Retreat Hot Tub, Fire Pit & Kayaks
Exterior

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is HK$744
HK$1,977 total
includes taxes & fees
1 Jun - 2 Jun
Charming "Cream of the Crop" Cape ~❤️of Middletown
1 bedroom, premium bedding, down duvets, laptop workspace

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (13 reviews)
"It was the perfect getaway with amazing views and relaxation."
United States
Natalie
The price is HK$2,490
HK$3,939 total
includes taxes & fees
21 Jun - 22 Jun
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is HK$1,567
HK$2,607 total
includes taxes & fees
7 Jun - 8 Jun
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is HK$1,484
HK$2,578 total
includes taxes & fees
1 Jun - 2 Jun
Forest chalet w/ hot tub & BBQ grill
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (17 reviews)
"The house was spotless, and exactly where we needed/wanted to be. It was close to everything we wanted to see and we definitely will use it again!"
United States
Janet L.
The price is HK$803
HK$2,139 total
includes taxes & fees
3 Jun - 4 Jun
Chic, pets, walk to downtown
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (22 reviews)
"Great view, very secluded"
United States
Matt s.
The price is HK$1,144
HK$3,467 total
includes taxes & fees
31 May - 1 Jun
Cottage w/ Hot Tub and 100-Mile Valley Views!
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (29 reviews)
"Great location, clean place. "
United States
Warren B.
The price is HK$691
HK$1,779 total
includes taxes & fees
8 Jun - 9 Jun
Cozy, dog-friendly, downtown
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, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

4/10 Poor
"The rooms have a weird odor to them."
Maheshwar 3-night trip
Posted 12 hours ago
Country Inn & Suites by Radisson, Frederick, MD

Find out more about Shepherdstown

Search for holiday rentals in Shepherdstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherdstown using one of the methods below:

  • View our selection of featured holiday rentals in Shepherdstown
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Look no further and take a look at our great range of rental properties in Shepherdstown!

Frequently asked questions

Are there holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What are some of the best holiday rentals that Shepherdstown has to offer?

Graycliff Retreat:Unforgettable experience at this 11BR Estate;Game Room+Hot tub: This highly rated holiday home rental in Shepherdstown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. Another good choice for your trip to Shepherdstown is Exclusive Wooded Chalet w Magnificent River Views.

How many holiday rentals will I find in Shepherdstown?

Expedia has 12 holiday rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Shepherdstown Public Library are other places worth a visit.

What’s a holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.