Shepherdstown Holiday Rentals

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Our top choices for Shepherdstown holiday rentals

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (67)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is NZ$182
includes taxes & fees
12 Jan - 13 Jan
❤️ Secluded 1940s Romantic Tiny House on the River

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (10)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is NZ$815
includes taxes & fees
20 Jan - 21 Jan
Exclusive Wooded Chalet w Magnificent River Views

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is NZ$324
includes taxes & fees
5 Jan - 6 Jan
Pet-friendly, heart of downtown

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (26)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$330
includes taxes & fees
4 Jan - 5 Jan
Cozy, dog-friendly, downtown

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is NZ$653
includes taxes & fees
8 Jan - 9 Jan
Aslan's How - Cabin with Valley Views & Hot Tub!

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
Cozy Pine Tree Nest

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (110)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is NZ$313
includes taxes & fees
5 Jan - 6 Jan
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
10.0 out of 10, Exceptional, (16)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is NZ$678
includes taxes & fees
6 Jan - 7 Jan
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (31)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
The price is NZ$634
includes taxes & fees
6 Jan - 7 Jan
Peaceful Lakefront Cottage with Mountain Views!

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
9.8 out of 10, Exceptional, (19)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
The price is NZ$245
includes taxes & fees
4 Jan - 5 Jan
Birch Cabin at Hunting Creek Hideaway

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Harpers Ferry
10.0 out of 10, Exceptional, (83)
"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"
United States
Sara S.
The price is NZ$474
includes taxes & fees
6 Jan - 7 Jan
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is NZ$278
includes taxes & fees
26 Jan - 27 Jan
Bring Your Own Boat - Meticulously restored house on the Potomac River

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (76)
"Great location and has exactly what you need to enjoy a stay in downtown Frederick!"
United States
Amy R.
The price is NZ$454
includes taxes & fees
3 Jan - 4 Jan
*Modern Condo In Downtown Frederick*

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Frederick
10.0 out of 10, Exceptional, (6)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is NZ$364
includes taxes & fees
4 Jan - 5 Jan
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

The Oculus - Huge Cabin with a Hot Tub!

The Oculus - Huge Cabin with a Hot Tub!
Harpers Ferry
9.6 out of 10, Exceptional, (25)
"Great stay "
United States
Seth W.
The price is NZ$753
includes taxes & fees
8 Jan - 9 Jan
The Oculus - Huge Cabin with a Hot Tub!

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (62)
"Always clean and comfortable home. Close to restaurants and shops but in quiet neighborhood to relax. Our second stay in this home. "
United States
Jelinda C.
The price is NZ$449
includes taxes & fees
4 Jan - 5 Jan
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (7)
"We had a great stay "
United States
Lauren O.
The price is NZ$935
includes taxes & fees
8 Jan - 9 Jan
Cozy Mountain Retreat | Hot Tub & Fire Pit & Dogs

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (71)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is NZ$441
includes taxes & fees
1 Feb - 2 Feb
*Luxury Condo In Downtown Frederick*

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (21)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
The price is NZ$624
includes taxes & fees
15 Jan - 16 Jan
Lake View Retreat - Cottage Near a Peaceful Lake!

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, (65)
"Great stay! We would book again. "
United States
Sam F.
The price is NZ$634
includes taxes & fees
6 Jan - 7 Jan
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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

Find out more about Shepherdstown

Everything you need to know about Shepherdstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shepherdstown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherdstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherdstown holiday rentals we have selected for you start as low as NZ$182 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shepherdstown has to offer?

Hot tub, Campfire ring and great location!: This holiday home rental outside of Shepherdstown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

How many holiday rentals will I find in Shepherdstown?

Expedia has 9 holiday 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 holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.