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

Shepherdstown Holiday Rentals

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Our top choices for Shepherdstown holiday rentals

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (79 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is NZ$241
includes taxes & fees
9 July - 10 July
❤️ Secluded 1940s Romantic Tiny House on the River

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (19 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is NZ$1,049
includes taxes & fees
5 July - 6 July
Exclusive Wooded Chalet w Magnificent River Views

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (68 reviews)
"Great stay! We would book again. "
United States
Sam F.
The price is NZ$705
includes taxes & fees
14 July - 15 July
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (39 reviews)
"It was my second time at Rebel’s Rest and it does not disappoint. The place is very clean, view is amazing, the kitchen is surprisingly equipped, and the Appalachian Trail is right up the street.Check-in went off without a hitch and communication was easy.I hope to be back soon."
United States
Matt P.
Rebels Rest - Cabin with Enchanting Sunset Views!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (93 reviews)
"Clean cozy cabin. Everything was clean and organized and easy to use. "
United States
John S.
The price is NZ$647
includes taxes & fees
27 July - 28 July
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

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, (13 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 NZ$331
includes taxes & fees
13 July - 14 July
Bring Your Own Boat - Meticulously restored house on the Potomac River

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, (102 reviews)
"This is a beautiful and peaceful property. I enjoyed my stay and will definitely book again. "
United States
Dianne F.
The price is NZ$477
includes taxes & fees
19 July - 20 July
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is NZ$713
includes taxes & fees
9 July - 10 July
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

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, (24 reviews)
"Great view, very secluded"
United States
Matt s.
The price is NZ$817
includes taxes & fees
15 July - 16 July
Cottage w/ Hot Tub and 100-Mile Valley Views!

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (72 reviews)
"We had such a lovely weekend staying here. Eddie, the property manager, was wonderful, check-in and check-out were incredibly easy, and the house was spotless. It truly felt like staying in a family home, and we were treated like family during our stay.The location is the perfect distance from Harpers Ferry, with great trails, delicious restaurants, and wineries nearby. The views from the house and surrounding area were absolutely out of this world, and we couldn’t have asked for a better place...
United States
Ashley M.
The price is NZ$638
includes taxes & fees
9 July - 10 July
Blue Ridge Getaway - Sunset Views, A.T. Access

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (64 reviews)
"The apartment was cozy and just as described. Check-in was super easy and the owners were very responsive to any questions we had. Thanks for a super pleasant stay!"
United States
Candi M.
The price is NZ$317
includes taxes & fees
7 July - 8 July
Cozy Getaway near Harper`s Ferry, C&O & Potomac

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, (38 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is NZ$819
includes taxes & fees
16 July - 17 July
Secluded Cabin a Stone's Throw From the A.T.!

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.4 out of 10, Exceptional, (91 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 NZ$575
includes taxes & fees
15 July - 16 July
Antietam Creek - Quiet 2 Bedroom Cabin

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
7.0 out of 10, Good, (10 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is NZ$440
includes taxes & fees
7 July - 8 July
2-Bedroom cabin Hot tub Fireplace PS5

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (67 reviews)
"We had 6 in our group and it was perfect especially for the price. Super clean, great responsive host, good location. Bakery directly across the street and ice cream and sandwich shop just down the road at the light. Will definitely stay here again. "
United States
Anonymous traveller
The price is NZ$437
includes taxes & fees
8 July - 9 July
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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
9.8 out of 10, Exceptional, (16 reviews)
"It was the perfect getaway with amazing views and relaxation."
United States
Natalie
The price is NZ$1,014
includes taxes & fees
9 July - 10 July
Mirror Villas - Modern Retreat with private hot tubs and mountain view

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, (130 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is NZ$508
includes taxes & fees
15 July - 16 July
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is NZ$595
includes taxes & fees
6 July - 7 July
Woodsy Retreat with a Hot Tub and Seasonal Views!

The Oculus - Huge Cabin with a Hot Tub!

The Oculus - Huge Cabin with a Hot Tub!
Harpers Ferry
9.6 out of 10, Exceptional, (30 reviews)
"We had a lovely weekend staying at Mountain Momma! The rooms were clean and the kitchen was great for cooking for a large group. "
United States
Mary C.
The price is NZ$776
includes taxes & fees
7 July - 8 July
The Oculus - Huge Cabin with a Hot Tub!

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.
Pet-friendly, heart of 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

Find out more about Shepherdstown

Everything you need to know about Shepherdstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherdstown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shepherdstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherdstown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherdstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherdstown holiday rentals we have selected for you start as low as NZ$241 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shepherdstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherdstown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherdstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This holiday home rental outside of Shepherdstown offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Shepherdstown?

Expedia has 11 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 Historic District 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.