Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
$122 nightly
The price is $135
May 19 - May 20
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)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
$433 nightly
The price is $470
May 14 - May 15
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
$165 nightly
The price is $175
May 13 - May 14
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$313 nightly
The price is $332
May 13 - May 14
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
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.
$214 nightly
The price is $227
May 18 - May 19
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, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$301 nightly
The price is $335
May 13 - May 14
Total with taxes and fees
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.
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, (63 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
$269 nightly
The price is $285
May 17 - May 18
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Interior

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (11 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.
$169 nightly
The price is $188
May 13 - May 14
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
TV, books

Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
Sleepy Hollow
8.6 out of 10, Excellent, (14 reviews)
"We had a lovely time staying here. It was comfortable and clean, and Tony was very responsive and helpful with the few things we needed. "
United States
Kasey L.
$265 nightly
The price is $285
May 18 - May 19
Total with taxes and fees
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
TV, foosball, books

Cozy Pine Tree Nest

Cozy Pine Tree Nest
Frederick
9.4 out of 10, Exceptional, (11 reviews)
"Peaceful studio with a lovely view off the porch. Was easy to find and all aspects of the stay were smooth. Perfect place for a few days in Frederick "
United States
Morgan P.
$160 nightly
The price is $170
May 17 - May 18
Total with taxes and fees
Cozy Pine Tree Nest

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, (126 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
$247 nightly
The price is $262
May 18 - May 19
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Interior

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Property was beautiful, and the hot tub was amazing! We will definitely book again!"
United States
KasiLyn D.
$347 nightly
The price is $396
May 13 - May 14
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.6 out of 10, Good, (27 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
$262 nightly
The price is $292
Jun 1 - Jun 2
Total with taxes and fees
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Outdoor dining

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (42 reviews)
"Immaculate apartment conveniently located close to Frederick Health Hospital in a quiet residential neighborhood. Just a fifteen minute walk to the heart of Frederick for memorable dining, interesting shops, and cozy cafés."
United States
Mark L.
$275 nightly
The price is $292
May 13 - May 14
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (22 reviews)
"Great view, very secluded"
United States
Matt s.
$342 nightly
The price is $381
May 27 - May 28
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.4 out of 10, Very Good, (5 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
$244 nightly
The price is $252
May 19 - May 20
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
TV

Inns of Whitetail #209

Inns of Whitetail #209
Mercersburg
10.0 out of 10, Exceptional, (3 reviews)
"Great stay for the time we were there, right off the slopes."
United States
Robert M.
$272 nightly
The price is $292
May 13 - May 14
Total with taxes and fees
Inns of Whitetail #209
Exterior

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (24 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
$189 nightly
The price is $200
May 13 - May 14
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Property grounds

Glamping Clear Spring Maryland 3-Cabin Campground

Glamping Clear Spring Maryland 3-Cabin Campground
Clear Spring
9.8 out of 10, Exceptional, (17 reviews)
"Absolutely amazing stay. Tom and Karen are amazing hosts. Cabins and property were spotless. Plenty of seating. Quiet and private and cant wait to go back again. Already planning next years weekend. Thank you for opening up your property to us all and treating us so well. "
United States
Christopher J.
$355 nightly
The price is $395
May 13 - May 14
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (29 reviews)
"Great location, clean place. "
United States
Warren B.
$206 nightly
The price is $218
May 13 - May 14
Total with taxes and fees
Cozy, dog-friendly, downtown
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

Tru By Hilton Martinsburg

Tru By Hilton Martinsburg

10/10 Excellent
"Very good breakfast choices. Pool table on the premises. "
Robert 1-night trip
Posted 8 hours ago
Tru By Hilton Martinsburg

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 $135 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.