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, (73 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AU$188
includes taxes & fees
27 Apr - 28 Apr
❤️ 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, (17 reviews)
"The entire stay was wonderful. Fantastic views. "
United States
Downer F.
The price is AU$646
includes taxes & fees
27 Apr - 28 Apr
Exclusive Wooded Chalet w Magnificent River Views

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, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is AU$302
includes taxes & fees
27 Apr - 28 Apr
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (86 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is AU$435
includes taxes & fees
20 Apr - 21 Apr
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is AU$352
includes taxes & fees
17 Apr - 18 Apr
Charming "Cream of the Crop" Cape ~❤️of Middletown

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 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is AU$228
includes taxes & fees
17 Apr - 18 Apr
Bring Your Own Boat - Meticulously restored house on the Potomac River

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (32 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
The price is AU$520
includes taxes & fees
20 Apr - 21 Apr
Rebels Rest - Cabin with Enchanting Sunset Views!

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is AU$202
includes taxes & fees
21 Apr - 22 Apr
Birch Cabin at Hunting Creek Hideaway

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is AU$269
includes taxes & fees
21 Apr - 22 Apr
Pet-friendly, heart of downtown

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (20 reviews)
"House was very clean and the hosts were responsive and very nice! Great place for a quiet weekend getaway. "
United States
Nicole H.
The price is AU$492
includes taxes & fees
20 Apr - 21 Apr
Log Cabin w/ Hot Tub & Waterfront Patio!

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, (67 reviews)
"Great home "
United States
January D.
The price is AU$509
includes taxes & fees
23 Apr - 24 Apr
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (99 reviews)
"Beautiful location! The host was extremely responsive with any questions most texts were returned within minutes! Will definitely stay here again. "
United States
Michael R.
The price is AU$339
includes taxes & fees
21 Apr - 22 Apr
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.6 out of 10, Exceptional, (45 reviews)
"The house was great, clean, beautiful setting."
United States
Brandon M.
The price is AU$492
includes taxes & fees
21 Apr - 22 Apr
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (66 reviews)
"Very quiet cabin. Nicely situated between Charles Town and Harper’s Ferry. "
United States
Kelly R.
The price is AU$577
includes taxes & fees
19 Apr - 20 Apr
Blue Ridge Getaway - Sunset Views, A.T. Access

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (125 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is AU$405
includes taxes & fees
20 Apr - 21 Apr
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
The price is AU$271
includes taxes & fees
21 Apr - 22 Apr
Cozy, dog-friendly, downtown

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 reviews)
"Amazing stay love this place very cozy house ."
United States
Aimee C.
The price is AU$295
includes taxes & fees
19 Apr - 20 Apr
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

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

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (35 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is AU$536
includes taxes & fees
30 Apr - 1 May
Secluded Cabin a Stone's Throw From the A.T.!

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"This was an amazing cabin with a full kitchen so you could cook and enjoy the quiet."
United States
Lina A.
The price is AU$460
includes taxes & fees
19 Apr - 20 Apr
Antietam Creek - Quiet 2 Bedroom Cabin

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (61 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is AU$351
includes taxes & fees
20 Apr - 21 Apr
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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 favourite 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 depend 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 AU$188 per night. Entering your travel dates in the search wizard might find you 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?

Exclusive Wooded Chalet w Magnificent River Views: This highly rated holiday home rental in Shepherdstown offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind.

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 Public Library 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.