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

Shepherdstown Vacation Rentals

Check prices for these dates

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

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
$127 nightly
The price is $141
Aug 31 - Sep 1
Total with taxes and fees
❤️ 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
$509 nightly
The price is $555
Sep 9 - Sep 10
Total with taxes and fees
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.
$257 nightly
The price is $286
Aug 12 - Aug 13
Total with taxes and fees
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.
$165 nightly
The price is $175
Aug 22 - Aug 23
Total with taxes and fees
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
$308 nightly
The price is $327
Sep 7 - Sep 8
Total with taxes and fees
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
$374 nightly
The price is $416
Aug 24 - Aug 25
Total with taxes and fees
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.
$305 nightly
The price is $340
Aug 13 - Aug 14
Total with taxes and fees
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, (95 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.
$315 nightly
The price is $334
Aug 12 - Aug 13
Total with taxes and fees
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.
$343 nightly
The price is $381
Aug 12 - Aug 13
Total with taxes and fees
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
$213 nightly
The price is $237
Aug 12 - Aug 13
Total with taxes and fees
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
$182 nightly
The price is $203
Aug 16 - Aug 17
Total with taxes and fees
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.
$436 nightly
The price is $462
Aug 12 - Aug 13
Total with taxes and fees
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.
$382 nightly
The price is $425
Aug 26 - Aug 27
Total with taxes and fees
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
$256 nightly
The price is $286
Aug 13 - Aug 14
Total with taxes and fees
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.
$296 nightly
The price is $330
Aug 13 - Aug 14
Total with taxes and fees
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.
$310 nightly
The price is $345
Aug 30 - Aug 31
Total with taxes and fees
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.
$171 nightly
The price is $190
Aug 12 - Aug 13
Total with taxes and fees
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. 4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
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.
$528 nightly
The price is $560
Aug 26 - Aug 27
Total with taxes and fees
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
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.
$237 nightly
The price is $251
Aug 13 - Aug 14
Total with taxes and fees
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"Perfect overnight stay. Everything was exactly as described. The breakfast was above and beyond."
Andrea 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Hagerstown

Find out more about Shepherdstown

Everything you need to know about Shepherdstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shepherdstown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Shepherdstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct: This vacation home rental near Shepherdstown offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.