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

1. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (82 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is NZ$239
includes taxes & fees
31 Aug - 1 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

2. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is NZ$1,232
includes taxes & fees
30 Aug - 31 Aug
Exclusive Wooded Chalet w Magnificent River Views

3. Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (209 reviews)
"Great place, pet friendly. "
United States
Doug P.
The price is NZ$297
includes taxes & fees
22 Aug - 23 Aug
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

4. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (2 reviews)
"The house is a perfect spot for walking to the battlefield"
United States
Karen
The price is NZ$556
includes taxes & fees
7 Sept - 8 Sept
Antietam House Historic Sharpsburg Retreat

5. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (96 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$554
includes taxes & fees
20 Aug - 21 Aug
Antietam Creek - Quiet 2 Bedroom Cabin

6. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is NZ$598
includes taxes & fees
1 Sept - 2 Sept
Antietam Look Out - Incredible Sunset Views!

7. 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, (72 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
The price is NZ$628
includes taxes & fees
24 Aug - 25 Aug
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

8. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is NZ$439
includes taxes & fees
17 Aug - 18 Aug
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

9. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is NZ$338
includes taxes & fees
19 Aug - 20 Aug
The Carriage House at Carrot Top Cottage

10. Rural Home, Hot Tub, Campfire, Hardwood Floors

Rural Home, Hot Tub, Campfire, Hardwood Floors
Harpers Ferry
9.4 out of 10, Exceptional, (86 reviews)
"We enjoyed this house very comfy cozy we stayed because we had a celebration of life and me and my family were able to just unwind here thank u so much we loved it and the jacuzzi was wonderful "
United States
Jennifer B.
The price is NZ$627
includes taxes & fees
19 Aug - 20 Aug
Rural Home, Hot Tub, Campfire, Hardwood Floors

11. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.4 out of 10, Very good, (63 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is NZ$766
includes taxes & fees
2 Sept - 3 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

12. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (42 reviews)
"Great location and very walkable to lower town. Parking was right outside of the unit which made it easy to load and unload all our belongings. Unit was very well appointed and had everything needed for a good stay."
United States
eric
The price is NZ$394
includes taxes & fees
17 Aug - 18 Aug
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

13. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (111 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is NZ$696
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

14. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (25 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
The price is NZ$894
includes taxes & fees
26 Aug - 27 Aug
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

15. Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (42 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is NZ$541
includes taxes & fees
24 Aug - 25 Aug
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

16. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Bolivar
10.0 out of 10, Exceptional, (57 reviews)
"Beautiful home; beds are very comfortable. Atmosphere very comforting. Kitchen well stocked. Would come again and will tell others great place to stay."
United States
Penny M.
The price is NZ$606
includes taxes & fees
27 Aug - 28 Aug
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"It’s the perfect river cabin to stay at. It’s older home so layout is awkward but it has been renovated and was nice and clean and perfect for our trip. Nice open dining/kitchen and living areas!! Host is AMAZING! She is so responsive and so helpful. We will definitely be back to stay!! "
United States
Amber W.
The price is NZ$319
includes taxes & fees
17 Aug - 18 Aug
Bring Your Own Boat - Meticulously restored house on the Potomac River

18. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.4 out of 10, Exceptional, (57 reviews)
"Great location. We'll kept up."
United States
Robert
The price is NZ$475
includes taxes & fees
20 Aug - 21 Aug
Best location! The Pullman Apt @ historic 1799 Inn

19. Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (114 reviews)
"The house was as advertised and served as a great location for our retreat! We had a freak plumbing emergency, and the host fixed it within literally an hour. "
United States
Connie V.
The price is NZ$977
includes taxes & fees
20 Aug - 21 Aug
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

20. Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (35 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
The price is NZ$549
includes taxes & fees
14 Sept - 15 Sept
Forest chalet w/ hot tub & BBQ grill
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shepherdstown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shepherdstown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shepherdstown. Seeing all the best attractions is bound to make you fall in love with Shepherdstown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shepherdstown short-term rentals, that won’t be hard to do.

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?

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.: This holiday home rental outside of Shepherdstown offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Shepherdstown?

Expedia has 9 holiday rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Museum and Shepherdstown Opera House, 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.