Holiday Rentals in Shepherdstown

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Holiday Rentals in Shepherdstown

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is €94
includes taxes & fees
1 Dec - 2 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin in Berkeley Springs

9.6 out of 10, Exceptional, (86)
"We loved this little cabin! It was so cozy and just 20-30 minutes from anything in town. "
United States
Gabrielle B.
Hidden Gem in the woods with hot tub

Cabin in Berkeley Springs

10.0 out of 10, Exceptional, (60)
"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"
United States
Robert Z.
Private, light filled retreat space... with your own pickleball court!

Chalet in Mercersburg

3.5 star property
9.6 out of 10, Exceptional, (4)
"Clean room, spacious intimate setting "
United States
Camille
The price is €516
includes taxes & fees
16 Dec - 17 Dec
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Holiday Home in Charles Town

9.6 out of 10, Exceptional, (65)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
United States
Cherilyn M.
The price is €358
includes taxes & fees
4 Dec - 5 Dec
Terra Alta - Incredible River Views and Hot Tub!

Holiday Home in Harpers Ferry

9.8 out of 10, Exceptional, (133)
"Although I never met my hostess, the cottage stay was easy to book and just as advertised. Fantastic views, well stocked kitchen, and a personal greeting on wet board. Gas fireplace was warm and cozy."
United States
Karen
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Cabin in Middletown

10.0 out of 10, Exceptional, (127)
"Great place to stay. Very quiet. Just wish there would have been a king size bed, otherwise loved it"
United States
Corinne R.
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Apartment in Harpers Ferry

9.4 out of 10, Exceptional, (20)
"Cute little place with a cabin feel, it had everything I needed and then some. The place was very clean, the bed was very comfortable, and the shower was clean and welcome after long hiking days. "
United States
Julie B.
The price is €174
includes taxes & fees
23 Nov - 24 Nov
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cottage in Berkeley Springs

10.0 out of 10, Exceptional, (16)
"Very clean and cozy place. Kitchen was well stocked with everything we need to cook with, open floor plan with a big cozy couch and big TV. "
United States
Richard M.
The price is €371
includes taxes & fees
29 Nov - 30 Nov
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Cabin in Middletown

9.6 out of 10, Exceptional, (105)
"We loved it! As cute/sweet as described."
United States
Fran E.
The price is €185
includes taxes & fees
24 Nov - 25 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cabin in Shepherdstown

9.6 out of 10, Exceptional, (39)
"My family enjoyed our stay at the cabin including having access to the river for morning coffee and playing board games in the evening after a day of tubing. The drive to the cabin was beautiful with lots of deer sightings. "
United States
Leana H.
The price is €225
includes taxes & fees
4 Dec - 5 Dec
Charming Cabin in the Woods with River Access

Holiday Home in Harpers Ferry

8.2 out of 10, Very good, (29)
"Very nice. Loved the location. Arcade did not work and no propane for the fire pit but overall amazing."
United States
Terry K.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Holiday Home in Harpers Ferry

9.8 out of 10, Exceptional, (105)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
United States
Debbie G.
The price is €483
includes taxes & fees
24 Nov - 25 Nov
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Holiday Home in Harpers Ferry

9.6 out of 10, Exceptional, (101)
"The house was beyond expectations."
United States
Eddie J.
The price is €366
includes taxes & fees
1 Dec - 2 Dec
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Holiday Home in Berkeley Springs

10.0 out of 10, Exceptional, (65)
"This place is amazing"
United States
Mike A.
Sleepy Creek - hot tub, pets, grill, fire pit, wifi, screen porch, creekside

Cabin in Charles Town

10.0 out of 10, Exceptional, (9)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is €291
includes taxes & fees
1 Dec - 2 Dec
The River House

Cabin in Harpers Ferry

9.2 out of 10, Wonderful, (9)
"Very charming and spacious silo! Very quiet and comfortable. Highly recommend and would definitely stay again!"
United States
Lauren M.
The price is €264
includes taxes & fees
24 Nov - 25 Nov
Wild And Wonderful Silos

Holiday Home in Berkeley Springs

10.0 out of 10, Exceptional, (45)
"What an absolutely gorgeous place with unbelievable views off the balcony! We really enjoyed our spring break there with lots of hiking outings and zip lining not too far away. "
United States
Cintia U.
✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

Cabin in Harpers Ferry

10.0 out of 10, Exceptional, (33)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is €348
includes taxes & fees
4 Dec - 5 Dec
Secluded Cabin a Stone's Throw From the A.T.!

Cabin in Harpers Ferry

9.2 out of 10, Wonderful, (62)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is €248
includes taxes & fees
3 Dec - 4 Dec
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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, apart-hotels, 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 €94 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?

Terra Alta - Incredible River Views and Hot Tub!: 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 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Shepherdstown?

Expedia has 10 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.