Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

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, (71 reviews)
"This trip was to celebrate my 64th birthday and wind down from my busy job It was perfect for both .. very relaxing, and very cozy. We'd love to stay again."
United States
Kaleb C
The price is ￥6,140
￥16,243 total
includes taxes & fees
Mar 2 - Mar 3
❤️ 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, (14 reviews)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
The price is ￥39,532
￥70,461 total
includes taxes & fees
Feb 23 - Feb 24
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, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
The price is ￥10,854
￥28,762 total
includes taxes & fees
Feb 25 - Feb 26
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (34 reviews)
"The cabin was very easy to get to, and yet it felt like you were in the middle of nowhere. The view was excellent. The accommodations were top-notch. I recommend this place to anyone."
United States
Greg R.
The price is ￥15,505
￥54,714 total
includes taxes & fees
Feb 23 - Feb 24
Antietam Look Out - Incredible Sunset Views!
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is ￥14,513
￥22,780 total
includes taxes & fees
Feb 23 - Feb 24
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)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is ￥8,094
￥28,302 total
includes taxes & fees
Feb 23 - Feb 24
Pet-friendly, heart of downtown
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 stay! We would book again. "
United States
Sam F.
The price is ￥15,505
￥56,441 total
includes taxes & fees
Feb 26 - Feb 27
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (63 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
The price is ￥18,001
￥40,119 total
includes taxes & fees
Feb 23 - Feb 24
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Interior

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (31 reviews)
"Gorgeous cabin, incredibly clean and well stocked with everything needed. Hot tub was amazing and clean and huge. Greatful for the hosts promptness in communication.Thank you!"
United States
Samantha S.
The price is ￥23,034
￥42,691 total
includes taxes & fees
Feb 23 - Feb 24
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
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.
The price is ￥11,629
￥24,994 total
includes taxes & fees
Feb 27 - Feb 28
Bring Your Own Boat - Meticulously restored house on the Potomac River
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (142 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥13,179
￥35,993 total
includes taxes & fees
Feb 26 - Feb 27
Charming "Cream of the Crop" Cape ~❤️of Middletown
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, (95 reviews)
"Love it been coming here for a few years now "
United States
Kristina M.
The price is ￥13,955
￥34,595 total
includes taxes & fees
Feb 23 - Feb 24
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
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.
The price is ￥9,475
￥31,574 total
includes taxes & fees
Feb 23 - Feb 24
Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown
Property grounds

Stone chalet w/ hot tub & views

Stone chalet w/ hot tub & views
Gerrardstown
9.2 out of 10, Wonderful, (39 reviews)
"The cabin was cozy. We enjoyed the fireplace nightly as well as the hot tub.The cabin was clean and the host was very responsive. "
United States
gail h.
The price is ￥23,729
￥48,835 total
includes taxes & fees
Mar 5 - Mar 6
Stone chalet w/ hot tub & views
1 bedroom, free WiFi, bed sheets

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is ￥9,210
￥29,484 total
includes taxes & fees
Feb 23 - Feb 24
Cozy, dog-friendly, downtown
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.
The price is ￥31,010
￥50,949 total
includes taxes & fees
Feb 23 - Feb 24
Antietam Creek - Quiet 2 Bedroom Cabin
Dining

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (77 reviews)
"Lovely place. It was perfect for our girls' trip long weekend. The rooms were so spacious and tastefully decorated. It was also super clean and had everything we needed, including for our night staying in with Door-dash to binge watch a couple Netflix series. The coffee lover in our group was so appreciative of the supplies and setup. The location is fabulous for walking the Creek Park, or to dinning and shopping options. We're looking forward to making this our Christmas present to each other...
United States
Lynne
The price is ￥15,815
￥40,266 total
includes taxes & fees
Feb 24 - Feb 25
*Luxury Condo In Downtown Frederick*
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, (59 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is ￥13,179
￥35,993 total
includes taxes & fees
Feb 23 - Feb 24
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Smart TV, fireplace

Peregrine's Perch - Cabin Overlooking the River!

Peregrine's Perch - Cabin Overlooking the River!
Falling Waters
9.6 out of 10, Exceptional, (21 reviews)
"Great place for a family weekend retreat. "
United States
Dina S.
The price is ￥19,226
￥60,866 total
includes taxes & fees
Mar 1 - Mar 2
Peregrine's Perch - Cabin Overlooking the River!
Outdoor spa tub

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi

Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi
Sleepy Hollow
9.2 out of 10, Wonderful, (9 reviews)
"Great location, perfect for a quick weekend getaway! "
United States
Kate C.
The price is ￥21,124
￥40,741 total
includes taxes & fees
Feb 23 - Feb 24
Secluded Cabin: Hot Tub, Huge Deck, Fire Pit, WiFi
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

Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

10/10 Excellent
"Staff were very courteous "
michele 3-night trip
Posted 4 days ago
Hilton Garden Inn Frederick

Find out more about Shepherdstown

Search for holiday rentals in Shepherdstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherdstown using one of the methods below:

  • View our selection of featured holiday rentals in Shepherdstown
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  • Enter your travel dates to view the best deals on holiday rentals in Shepherdstown while they last

Look no further and take a look at our great range of rental properties in Shepherdstown!

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?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This vacation home near Shepherdstown offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Shepherdstown?

Expedia has 9 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 Rumsey Steamboat Museum 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.