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

Shepherdstown Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$96 nightly
The price is $107
Oct 25 - Oct 26
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)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
$199 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
$290 nightly
The price is $313
Oct 18 - Oct 19
Total with taxes and fees
Charming Shepherdstown Home - Walk to Downtown
Terrace/patio

4. 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
Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

5. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
Walk to Stores: Home in Historic Shepherdstown!
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

6. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
$252 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
Charming Cabin in the Woods with River Access
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, (76 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$350 nightly
The price is $390
Nov 3 - Nov 4
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A room with large windows, wooden floors, and a ceiling fan.

8. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
$313 nightly
The price is $332
Oct 18 - Oct 19
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A bedroom with a bed, a table, and a view of the outdoors.

9. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$198 nightly
The price is $221
Nov 9 - Nov 10
Total with taxes and fees
The Carriage House at Carrot Top Cottage
A dining area with a white table and chairs, a fireplace, and a glass coffee table with a magazine.

10. Best location! The Ohio Suite @ historic 1799 Inn

Best location! The Ohio Suite @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (21 reviews)
"Perfect location and the accommodations were inviting, roomy and comfortable. We had a wonderful stay and were very pleased with the suite."
United States
michele b.
$220 nightly
The price is $245
Nov 1 - Nov 2
Total with taxes and fees
Best location! The Ohio Suite @ historic 1799 Inn
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

11. 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, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
$261 nightly
The price is $291
Oct 18 - Oct 19
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

12. Schilling House

Schilling House
3.0 star property
Bolivar
$299 nightly
The price is $320
Oct 26 - Oct 27
Total with taxes and fees
Schilling House
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

13. 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
$206 nightly
The price is $229
Nov 1 - Nov 2
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

14. 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, (55 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.
$228 nightly
The price is $254
Oct 19 - Oct 20
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A deck with green chairs and a fire pit, surrounded by a house and trees.

15. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (32 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
$480 nightly
The price is $509
Oct 18 - Oct 19
Total with taxes and fees
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A two-story house with a porch, green shutters, and a red roof.

16. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (58 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
$368 nightly
The price is $387
Oct 21 - Oct 22
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

17. 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.
$323 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

18. 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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
$275 nightly
The price is $306
Oct 21 - Oct 22
Total with taxes and fees
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
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.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (34 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 3 - Nov 4
Total with taxes and fees
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

20. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location and property."
United States
Helen F.
$276 nightly
The price is $307
Nov 13 - Nov 14
Total with taxes and fees
Hidden Creekside retreat near 5 national parks, including 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

Quality Inn Shepherdstown

Quality Inn Shepherdstown

10/10 Excellent
"Great"
Terry 1-night trip
Posted 17 hours ago
Quality Inn Shepherdstown

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 $107 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.

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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.