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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Shepherdstown vacation rentals

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$101 nightly
The price is $112
Oct 8 - Oct 9
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A living room with a dining table, chairs, a sofa, and a television.

2. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
$231 nightly
The price is $257
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A window with a view of a grassy yard and trees.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
$256 nightly
The price is $275
Oct 14 - Oct 15
Total with taxes and fees
Charming Shepherdstown Home - Walk to Downtown
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
$665 nightly
The price is $726
Oct 14 - Oct 15
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Terrace/patio

5. Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia

Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
Shepherdstown
$915 nightly
The price is $970
Oct 14 - Oct 15
Total with taxes and fees
Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
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, (98 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.
$311 nightly
The price is $330
Oct 4 - Oct 5
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

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
$401 nightly
The price is $446
Oct 28 - Oct 29
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

8. Schilling House

Schilling House
3.0 star property
Bolivar
$321 nightly
The price is $343
Oct 4 - Oct 5
Total with taxes and fees
Schilling House
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

9. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$342 nightly
The price is $381
Oct 14 - Oct 15
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A wooden pergola with a sofa and chairs underneath, surrounded by potted plants.

10. Petite Retreat at Harper's Ferry

Petite Retreat at Harper's Ferry
Bolivar
$234 nightly
The price is $236
Oct 4 - Oct 5
Total with taxes and fees
Petite Retreat at Harper's Ferry
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, (48 reviews)
"Rental was exactly as advertised and in a great location within walking distance of a lot of great spots to check out."
United States
Sarah D.
$226 nightly
The price is $252
Oct 4 - Oct 5
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

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, (48 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
$259 nightly
The price is $289
Oct 8 - Oct 9
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A bedroom with a bed, a table, and a view of the outdoors.

13. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (53 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.
$197 nightly
The price is $220
Nov 1 - Nov 2
Total with taxes and fees
The Carriage House at Carrot Top Cottage
A teepee with a sleeping area and a hot tub.

14. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
$321 nightly
The price is $332
Oct 4 - Oct 5
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (60 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
$204 nightly
The price is $227
Nov 1 - Nov 2
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A four-poster canopy bed with a view of a cityscape through the window.

16. 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
Oct 4 - Oct 5
Total with taxes and fees
Eclectic & Romantic - Walk to Historic Downtown 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.

17. 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, (63 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.
$236 nightly
The price is $263
Nov 1 - Nov 2
Total with taxes and fees
Top o' the Hill Apt. in historic Harpers Ferry
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.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 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.
$305 nightly
The price is $340
Nov 1 - Nov 2
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A two-story house with a porch, green shutters, and a red roof.

19. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (57 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
$410 nightly
The price is $432
Oct 4 - Oct 5
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

20. 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, (69 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
$169 nightly
The price is $179
Oct 13 - Oct 14
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
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

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

10/10 Excellent
"Overall great place to stay and if i come back I will stay there again. Room was modern and clean. The staff was friendly."
TIMOTHY 2-night trip
Posted 6 hours ago
Quality Inn Harpers Ferry - Charles Town

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 $112 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?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Shepherdstown is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease 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 10 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.