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

Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Shepherdstown vacation rentals

Exterior

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 SAR 270
SAR 530 total
includes taxes & fees
7 Sep - 8 Sep
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

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 SAR 1,214
SAR 2,038 total
includes taxes & fees
9 Sep - 10 Sep
Exclusive Wooded Chalet w Magnificent River Views
Property grounds

3. 5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (50 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Exterior

4. 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 SAR 544
SAR 661 total
includes taxes & fees
24 Aug - 25 Aug
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Interior

5. 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 SAR 537
SAR 1,226 total
includes taxes & fees
7 Sep - 8 Sep
Antietam House Historic Sharpsburg Retreat
TV, fireplace

6. 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 SAR 432
SAR 1,470 total
includes taxes & fees
31 Aug - 1 Sep
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Property grounds

7. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (53 reviews)
"Loved the place and area."
United States
Steve R.
Charming Cabin in the Woods with River Access
Interior

8. 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 SAR 751
SAR 1,246 total
includes taxes & fees
20 Aug - 21 Aug
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

9. 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.
Rural Home, Hot Tub, Campfire, Hardwood Floors
Interior

10. 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 SAR 544
SAR 958 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
1 bedroom, WiFi, bed sheets

11. 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 SAR 465
SAR 761 total
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Carrot Top Cottage
Interior

12. 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 SAR 848
SAR 1,822 total
includes taxes & fees
8 Sep - 9 Sep
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Smart TV, fireplace, DVD player, books

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 SAR 478
SAR 1,559 total
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

14. 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 SAR 673
SAR 1,072 total
includes taxes & fees
27 Aug - 28 Aug
Best location! The Pullman Apt @ historic 1799 Inn
Terrace/patio

15. 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, (56 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 SAR 597
SAR 1,364 total
includes taxes & fees
24 Aug - 25 Aug
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Terrace/patio

16. 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 SAR 568
SAR 1,339 total
includes taxes & fees
20 Aug - 21 Aug
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Interior

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 SAR 372
SAR 714 total
includes taxes & fees
16 Aug - 17 Aug
Bring Your Own Boat - Meticulously restored house on the Potomac River
Outdoor dining

18. New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Terrace/patio

19. Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – Harpers Ferry

Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – 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 SAR 730
SAR 2,103 total
includes taxes & fees
26 Aug - 27 Aug
Modern Retreat - 4 King Suites, Saltwater Hot Tub & Game Room – Harpers Ferry
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (153 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is SAR 601
SAR 1,254 total
includes taxes & fees
24 Aug - 25 Aug
Charming "Cream of the Crop" Cape ~❤️of Middletown
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

Days Inn by Wyndham Frederick

Days Inn by Wyndham Frederick

8/10 Good
"It was clean and generally comfortable, but The breakfast was not good: very limited options. There were 2 bins of cereal, one of which had a mixture of fruity pebbles, captain crunch, lucky charms, and probably a couple other random cereals in it. Like they just dumped in whatever… there were packets of instant oatmeal that were solidified."
Wendy 1-night trip
Posted 16 hours ago
Days Inn by Wyndham Frederick

Frequently asked questions

Are there vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to 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's the top vacation rental in Shepherdstown?

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.: This vacation home rental near Shepherdstown offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Shepherdstown?

Expedia has 9 vacation 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 vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.