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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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
9.6 out of 10, Exceptional, (80 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$127 nightly
The price is $141
Aug 24 - Aug 25
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
$622 nightly
The price is $679
Aug 23 - Aug 24
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, (47 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.
$259 nightly
The price is $288
Aug 2 - Aug 3
Total with taxes and fees
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
TV, fireplace

4. 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, (70 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$379 nightly
The price is $422
Aug 13 - Aug 14
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Property grounds

5. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (51 reviews)
"Loved the place and area."
United States
Steve R.
$301 nightly
The price is $335
Aug 2 - Aug 3
Total with taxes and fees
Charming Cabin in the Woods with River Access
Interior

6. 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.
$313 nightly
The price is $332
Aug 3 - Aug 4
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

7. 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.
$399 nightly
The price is $423
Aug 2 - Aug 3
Total with taxes and fees
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Exterior

8. 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, (65 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.
$169 nightly
The price is $179
Aug 5 - Aug 6
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Smart TV, fireplace, DVD player, books

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

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 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.
$350 nightly
The price is $390
Aug 2 - Aug 3
Total with taxes and fees
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
1 bedroom, WiFi, bed sheets

10. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (51 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$181 nightly
The price is $202
Aug 3 - Aug 4
Total with taxes and fees
The Carriage House at Carrot Top Cottage
Property grounds

11. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
$337 nightly
The price is $375
Aug 17 - Aug 18
Total with taxes and fees
Cabin at the Gap | You Won't Believe the View!
Terrace/patio

12. 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.
$308 nightly
The price is $343
Aug 9 - Aug 10
Total with taxes and fees
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Interior

13. 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)
"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.
$169 nightly
The price is $188
Aug 3 - Aug 4
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
Outdoor spa tub

14. Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Harpers Ferry
9.6 out of 10, Exceptional, (19 reviews)
"The house was clean and accommodating. It was truly right next door to the river riders establishment. The hot tub was AMAZING! Wish I had more time to enjoy it. We would definitely rent it again "
United States
Lynette M.
$359 nightly
The price is $400
Aug 10 - Aug 11
Total with taxes and fees
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Interior

15. 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, (41 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
$206 nightly
The price is $230
Aug 18 - Aug 19
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Exterior

16. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"We had a great time. It was a great location to be close to the aid station for the C&O ultra. Great coffee shop nearby. It was comfortable and nice. Owners were very communicative."
United States
Angele C.
$233 nightly
The price is $247
Aug 2 - Aug 3
Total with taxes and fees
Historic Getaway near C&O Canal, hiking and biking
Terrace/patio

17. 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, (54 reviews)
"We appreciated the excellent communication with our host, spotless accommodations, bright lighting, well-appointed kitchen—and the provided coffee. "
United States
Cara B.
$326 nightly
The price is $363
Aug 2 - Aug 3
Total with taxes and fees
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Exterior

18. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (26 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
$187 nightly
The price is $198
Aug 2 - Aug 3
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
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.
$553 nightly
The price is $586
Aug 26 - Aug 27
Total with taxes and fees
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Hi Speed Internet
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

Tru By Hilton Hagerstown

Tru By Hilton Hagerstown

8/10 Good
"WiFi did not work in lobby."
Mark 1-night trip
Posted 4 hours ago
Tru By Hilton 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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home rental near Shepherdstown offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 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 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.