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

Shepherdstown Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
$198 nightly
The price is $220
Nov 1 - Nov 2
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 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
Nov 8 - Nov 9
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A living room with two leather sofas, a coffee table, and a brick wall.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
$314 nightly
The price is $338
Nov 2 - Nov 3
Total with taxes and fees
Charming Shepherdstown Home - Walk to Downtown
A wooden deck with a grill, outdoor seating, and a bottle of wine.

4. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (54 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.
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

5. 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.
$254 nightly
The price is $282
Nov 12 - Nov 13
Total with taxes and fees
Charming Cabin in the Woods with River Access
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, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
$339 nightly
The price is $359
Oct 29 - Oct 30
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, (77 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$389 nightly
The price is $432
Nov 3 - Nov 4
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

8. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
$344 nightly
The price is $383
Nov 4 - Nov 5
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A spacious living room with a large window, a wooden coffee table, and a sofa.

9. Schilling House

Schilling House
3.0 star property
Bolivar
$321 nightly
The price is $343
Oct 29 - Oct 30
Total with taxes and fees
Schilling House
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

10. 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
10.0 out of 10, Exceptional, (52 reviews)
"Very clean Very convenient Very nice stay"
United States
Kevin
$271 nightly
The price is $302
Nov 2 - Nov 3
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
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, (56 reviews)
"We had a wonderful stay: The place was adorable, spotless, and had everything we needed for a relaxing getaway. It was cozy, well-maintained, and in a great location for exploring Harper’s Ferry. We’re staying here again in a couple months!"
United States
Hannah P.
$210 nightly
The price is $233
Oct 29 - Oct 30
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

12. 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, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
$429 nightly
The price is $455
Nov 4 - Nov 5
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A deck with green chairs and a fire pit, surrounded by a house and trees.

13. 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, (34 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
$456 nightly
The price is $484
Oct 29 - Oct 30
Total with taxes and fees
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – 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.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (35 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 bedroom with a bed, a table, and a view of the outdoors.

15. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$199 nightly
The price is $222
Nov 9 - Nov 10
Total with taxes and fees
The Carriage House at Carrot Top Cottage
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, (59 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
$392 nightly
The price is $412
Oct 29 - Oct 30
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

17. 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, (16 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
$423 nightly
The price is $471
Nov 9 - Nov 10
Total with taxes and fees
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A hammock on a grassy area with a view of a river and forested hills.

18. 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.
$416 nightly
The price is $463
Nov 11 - Nov 12
Total with taxes and fees
La Soledad Lavender Farm on the Potomac
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (61 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 4 - Nov 5
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
A living room with a TV displaying streaming services, a dining area with a table and chairs, a potted plant, and a wooden cabinet.

20. 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, (64 reviews)
"Clean and welcoming with adequate parking for all guests."
United States
Linda
$238 nightly
The price is $265
Nov 3 - Nov 4
Total with taxes and fees
Top o' the Hill Apt. 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherdstown Hotel Reviews

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"My room was amazing! modern, attractive and clean. The firmness of the bed was perfect. I slept well."
Malika 1-night trip
Posted 3 hours ago
Best Western Historic Frederick

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.

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.