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

Shepherdstown Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Shepherdstown vacation rentals

Dining

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (23 reviews)
"Host let us in a bit early which was nice!"
United States
John
$200 nightly
The price is $223
Aug 31 - Sep 1
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
Exterior

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$120 nightly
The price is $133
Sep 7 - Sep 8
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

3. 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
$451 nightly
The price is $491
Sep 7 - Sep 8
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Property grounds

4. 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.
$229 nightly
The price is $255
Sep 1 - Sep 2
Total with taxes and fees
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Exterior

5. 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, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
$166 nightly
The price is $176
Aug 31 - Sep 1
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

6. 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
Sep 6 - Sep 7
Total with taxes and fees
Charming Cabin in the Woods with River Access
TV, fireplace

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, (75 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$329 nightly
The price is $366
Aug 31 - Sep 1
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior

8. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$323 nightly
The price is $359
Sep 1 - Sep 2
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Interior

9. 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.
$315 nightly
The price is $334
Sep 1 - Sep 2
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Microwave, oven, stovetop, dishwasher

10. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
$429 nightly
The price is $455
Sep 7 - Sep 8
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Terrace/patio

11. 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, (58 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
$264 nightly
The price is $294
Aug 31 - Sep 1
Total with taxes and fees
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Terrace/patio

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

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (44 reviews)
"Great place to stay for the weekend."
United States
Bea G.
$276 nightly
The price is $307
Sep 13 - Sep 14
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Property grounds

13. La Soledad Lavender Farm on the Potomac

La Soledad Lavender Farm on the Potomac
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Terrific place and very friendly and accommodating host"
United States
Michel R.
$389 nightly
The price is $433
Sep 7 - Sep 8
Total with taxes and fees
La Soledad Lavender Farm on the Potomac
Exterior

14. Schilling House

Schilling House
3.0 star property
Bolivar
$310 nightly
The price is $331
Aug 30 - Aug 31
Total with taxes and fees
Schilling House
2 bedrooms, travel crib, WiFi, bed sheets

15. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Great spot"
China
Clara
$280 nightly
The price is $312
Aug 31 - Sep 1
Total with taxes and fees
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Interior

16. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
$335 nightly
The price is $373
Aug 30 - Aug 31
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Smart TV, fireplace

17. A private home in historic Bolivar with a hot tub and yard. Pet friendly!

A private home in historic Bolivar with a hot tub and yard. Pet friendly!
Bolivar
10.0 out of 10, Exceptional, (34 reviews)
"Lovely place to stay! "
United States
April O.
$361 nightly
The price is $402
Aug 31 - Sep 1
Total with taxes and fees
A private home in historic Bolivar with a hot tub and yard. Pet friendly!
Interior

18. Top o' the Hill Apt. in historic Harpers Ferry

Top o' the Hill Apt. in historic Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (60 reviews)
"Beautifully decorated and very clean. Perfect for our short stay. Parking was great and location was excellent. The guidebook for the stay was very comprehensive and convenient- had all information needed. Would highly recommend!"
United States
Jennifer H.
$284 nightly
The price is $316
Aug 31 - Sep 1
Total with taxes and fees
Top o' the Hill Apt. in historic Harpers Ferry
Interior

19. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
$400 nightly
The price is $446
Aug 30 - Aug 31
Total with taxes and fees
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Interior

20. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.4 out of 10, Exceptional, (43 reviews)
"We loved our stay, very cozy "
United States
Scot G.
$213 nightly
The price is $237
Aug 30 - Aug 31
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
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

The Plaza Inn & Suites

The Plaza Inn & Suites

10/10 Excellent
"Staff was great and the stay was awesome"
Donna 1-night trip
Posted 10 hours ago
The Plaza Inn & Suites

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 $133 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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This vacation home rental near Shepherdstown is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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.