Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Shepherdstown vacation rentals

Exterior

❤️ 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.
$120 nightly
The price is $133
Apr 27 - Apr 28
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (18 reviews)
"The entire stay was wonderful. Fantastic views. "
United States
Downer F.
$433 nightly
The price is $470
Apr 26 - Apr 27
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Interior

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.
$205 nightly
The price is $217
Apr 27 - Apr 28
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Dining

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.
$277 nightly
The price is $308
Apr 20 - Apr 21
Total with taxes and fees
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
Exterior

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.
$237 nightly
The price is $251
Apr 19 - Apr 20
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Interior

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.
$145 nightly
The price is $161
Apr 19 - Apr 20
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
Terrace/patio

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
$339 nightly
The price is $377
Apr 20 - Apr 21
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (26 reviews)
"We had a very nice stay here, kitchen and bathroom had all necessary amenities provided. Cozy cabin, a little chilly at night but blankets were provided as well so it was OK."
United States
Emily Z.
$135 nightly
The price is $143
Apr 21 - Apr 22
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway
Smart TV

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.
$183 nightly
The price is $194
Apr 21 - Apr 22
Total with taxes and fees
Pet-friendly, heart of downtown
Dining

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.
$315 nightly
The price is $351
Apr 20 - Apr 21
Total with taxes and fees
Log Cabin w/ Hot Tub & Waterfront Patio!
TV, fireplace

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.
$325 nightly
The price is $362
Apr 23 - Apr 24
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Property grounds

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.
$214 nightly
The price is $237
Apr 21 - Apr 22
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Dining

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.
$315 nightly
The price is $351
Apr 21 - Apr 22
Total with taxes and fees
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Smart TV, fireplace

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.
$357 nightly
The price is $397
Apr 19 - Apr 20
Total with taxes and fees
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.
$273 nightly
The price is $289
Apr 19 - Apr 20
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
1 bedroom, free WiFi, bed sheets

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.
$179 nightly
The price is $190
Apr 21 - Apr 22
Total with taxes and fees
Cozy, dog-friendly, downtown
Fridge, microwave, coffee/tea maker, toaster

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.
$195 nightly
The price is $207
Apr 19 - Apr 20
Total with taxes and fees
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Smart TV, fireplace

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.
$350 nightly
The price is $390
Apr 19 - Apr 20
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
Interior

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.
$310 nightly
The price is $329
Apr 19 - Apr 20
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Fridge, microwave, oven, stovetop

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.
$239 nightly
The price is $253
Apr 20 - Apr 21
Total with taxes and fees
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

Quality Inn Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

8/10 Good
"Excellent location and the breakfast was great. Staff were very friendly and parking was plentiful. All in all a good stay."
Brett 1-night trip
Posted 1 hour ago
Quality Inn Harpers Ferry - Charles Town

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 $133 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?

Exclusive Wooded Chalet w Magnificent River Views: Visitors give good reviews to this Shepherdstown vacation home rental, which offers a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 Public Library 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.