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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Shepherdstown vacation rentals

A living room with a dining table, chairs, a sofa, and a television.

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
$198 nightly
The price is $220
Sep 14 - Sep 15
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A spacious living room with a staircase, a sofa, a television, and a large window.

2. BEST LOCATION: Historic Shepherdstown Getaway

BEST LOCATION: Historic Shepherdstown Getaway
Shepherdstown
10.0 out of 10, Exceptional, (111 reviews)
"Wonderful host, great location, everything was a expected"
United States
Dave D.
$384 nightly
The price is $431
Sep 28 - Sep 29
Total with taxes and fees
BEST LOCATION: Historic Shepherdstown Getaway
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (85 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$99 nightly
The price is $110
Oct 5 - Oct 6
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A house with a deck, outdoor seating, and a fire pit.

4. 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
$624 nightly
The price is $681
Sep 22 - Sep 23
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
A hallway with wooden flooring, a ceiling fan, and a door leading to a room with a bed.

5. Schilling House

Schilling House
3.0 star property
Bolivar
$316 nightly
The price is $338
Sep 20 - Sep 21
Total with taxes and fees
Schilling House
A room with large windows, wooden floors, and a ceiling fan.

6. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
$310 nightly
The price is $329
Sep 13 - Sep 14
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A two-story house with a porch, green shutters, and a red roof.

7. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (55 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
$361 nightly
The price is $380
Sep 13 - Sep 14
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

8. 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
$328 nightly
The price is $365
Sep 14 - Sep 15
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (32 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.
$331 nightly
The price is $369
Sep 13 - Sep 14
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A dining area with a glass table surrounded by chairs, a living room in the background, and a window with white curtains.

10. Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!
Harpers Ferry
10.0 out of 10, Exceptional, (43 reviews)
"We loved this property! It was a perfect distance to the shops and restaurants in Harper’s Ferry. The house is beautiful and comfortable and even had some perks for our dog."
United States
Melissa V.
$401 nightly
The price is $447
Sep 13 - Sep 14
Total with taxes and fees
Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

11. 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, (47 reviews)
"We loved our stay, very cozy "
United States
Scot G.
$210 nightly
The price is $233
Sep 13 - Sep 14
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A living room with a TV displaying streaming services, a dining area with a table and chairs, a potted plant, and a wooden cabinet.

12. 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, (62 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.
$280 nightly
The price is $312
Sep 13 - Sep 14
Total with taxes and fees
Top o' the Hill Apt. in historic Harpers Ferry
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

13. 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)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
$429 nightly
The price is $455
Sep 27 - Sep 28
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (59 reviews)
"Great location. We'll kept up."
United States
Robert
$253 nightly
The price is $282
Sep 13 - Sep 14
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A two-story house with a porch, a brick chimney, and a garden area.

15. Hillside Hideaway in Lowertown Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (23 reviews)
"Perfect location for a visit to Harper’s Ferry "
United States
Evelyn C.
$463 nightly
The price is $516
Sep 13 - Sep 14
Total with taxes and fees
Hillside Hideaway in Lowertown Harpers Ferry
A modern living room with a sofa, chairs, a coffee table, and a TV on a stand.

16. 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.
$357 nightly
The price is $397
Sep 13 - Sep 14
Total with taxes and fees
A private home in historic Bolivar with a hot tub and yard. Pet friendly!
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

17. 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.
$332 nightly
The price is $370
Sep 22 - Sep 23
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

18. Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (12 reviews)
"Clean, great communication, amazing location. Don’t hesitate book it! I loved every aspect of this cozy place. "
United States
Tara
$273 nightly
The price is $304
Sep 13 - Sep 14
Total with taxes and fees
Best location! Baltimore Suite @ historic 1799 Inn
A four-poster canopy bed with a view of a cityscape through the window.

19. 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
$277 nightly
The price is $309
Sep 15 - Sep 16
Total with taxes and fees
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
A bedroom with a bed, a table, and a view of the outdoors.

20. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful location. Very peaceful and convenient for everything we wanted to do on our trip. Enjoyed all the deer while sitting outside the cottage reading."
United States
Clinton R.
$195 nightly
The price is $217
Sep 15 - Sep 16
Total with taxes and fees
The Carriage House at Carrot Top Cottage
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

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Great stay"
Michelle 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Frederick, MD

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 $110 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?

A peaceful, forest retreat with stunning views near historic 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 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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.