Shepherdstown Holiday Rentals

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Holiday Rentals in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is NZ$193
includes taxes & fees
1 Dec - 2 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Hidden Gem in the woods with hot tub

Berkeley Springs
9.6 out of 10, Exceptional, (86)
"Beautiful cabin. Updated photos are accurate but the space is even bigger in person. Hot tub and fire pit were great. House is clean and well equipped. Would stay again in a heartbeat. "
United States
Paul P.
Hidden Gem in the woods with hot tub

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs
10.0 out of 10, Exceptional, (59)
"We loved this place! The view was beautiful. Enjoyed the pickleball court. Would highly recommend it to anyone looking for a relaxing getaway!"
United States
Denise H.
Private, light filled retreat space... with your own pickleball court!

Mirror Villas - Modern Retreat with private hot tubs and mountain view

3.5 star property
Mercersburg
9.6 out of 10, Exceptional, (4)
"Clean room, spacious intimate setting "
United States
Camille
The price is NZ$1,084
includes taxes & fees
9 Dec - 10 Dec
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
9.6 out of 10, Exceptional, (65)
"I recommend this house for the Harpers Ferry location. Four spacious bedrooms, three bathrooms, hot tub, and games."
United States
joshua s.
The price is NZ$713
includes taxes & fees
4 Dec - 5 Dec
Terra Alta - Incredible River Views and Hot Tub!

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Harpers Ferry
9.8 out of 10, Exceptional, (132)
"Nice quaint cottage, perfect for our visit to the area. "
United States
Diane C.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Middletown
10.0 out of 10, Exceptional, (127)
"Great location. Very quick responses to texts. Susan checked in every day."
United States
Diane M.
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Harpers Ferry
9.4 out of 10, Exceptional, (20)
"Good location for visiting historic town. Freshly remodeled. Comfortable for couple or family with child."
United States
chad
The price is NZ$330
includes taxes & fees
18 Nov - 19 Nov
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Berkeley Springs
10.0 out of 10, Exceptional, (16)
"This is a very comfortable, quiet, and clean home, easily accessible by GPS. Great for our family of 6 with plenty of room and the home is stocked with essentials and conveniences (books, games, extra air mattress, crib, booster seat, etc.) Would definitely stay again for a get away to Berkeley Springs."
United States
Margaret Z.
The price is NZ$736
includes taxes & fees
18 Nov - 19 Nov
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

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

Middletown
9.6 out of 10, Exceptional, (105)
"Very cute cottage, filled with rustic charm. Convenient to hiking in Catoctin and restaurants in Frederick. AC worked great on a hot weekend! No door on the bathroom, just a curtain, FYI!"
United States
Cate O.
The price is NZ$379
includes taxes & fees
21 Nov - 22 Nov
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Charming Cabin in the Woods with River Access

Shepherdstown
9.6 out of 10, Exceptional, (38)
"Loved the cabin and seclusion. Would come back for sure. "
United States
Mark S.
The price is NZ$448
includes taxes & fees
19 Nov - 20 Nov
Charming Cabin in the Woods with River Access

Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Harpers Ferry
8.2 out of 10, Very good, (29)
"We had a great time "
United States
Robert M.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry
9.8 out of 10, Exceptional, (105)
"So close to River Riders Adventures and the National Historic Park."
United States
Philip B.
The price is NZ$1,000
includes taxes & fees
24 Nov - 25 Nov
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry
9.6 out of 10, Exceptional, (101)
"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"
United States
Jennifer L.
The price is NZ$731
includes taxes & fees
18 Nov - 19 Nov
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Sleepy Creek - hot tub, pets, grill, fire pit, wifi, screen porch, creekside

Berkeley Springs
10.0 out of 10, Exceptional, (65)
"Perfect getaway "
United States
Andrea F.
Sleepy Creek - hot tub, pets, grill, fire pit, wifi, screen porch, creekside

The River House

Charles Town
10.0 out of 10, Exceptional, (9)
"Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!"
United States
Casey W.
The price is NZ$565
includes taxes & fees
18 Nov - 19 Nov
The River House

Wild And Wonderful Silos

Harpers Ferry
9.6 out of 10, Exceptional, (8)
"Very nice place. Staying in a silo was a unique experience. It snowed while we were there and it was beautiful. We would definitely stay again. There is a lot to see and do in Harper's Ferry and the surrounding area."
United States
Teresa B.
The price is NZ$528
includes taxes & fees
18 Nov - 19 Nov
Wild And Wonderful Silos

✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

Berkeley Springs
10.0 out of 10, Exceptional, (45)
"Great house "
United States
bryan N.
✨Luxurious Mountaintop Lodge🏔️WOW Scenic Views🫧Hot Tub under the BIG SKY STARS 🌟

Secluded Cabin a Stone's Throw From the A.T.!

Harpers Ferry
10.0 out of 10, Exceptional, (33)
"We were charmed by the house and pleased with all the amenities. We would definitely stay there again. "
United States
Jennifer T.
The price is NZ$695
includes taxes & fees
18 Nov - 19 Nov
Secluded Cabin a Stone's Throw From the A.T.!

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Harpers Ferry
9.2 out of 10, Wonderful, (62)
"We had a get-together with our bridal party folks from out of town, and this was a great place to relax and play games. Cute decor, nice amenities. "
United States
Ashley Lynn C.
The price is NZ$471
includes taxes & fees
18 Nov - 19 Nov
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, 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$193 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.