Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

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, (72 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
Apr 14 - Apr 15
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, (17 reviews)
"The entire stay was wonderful. Fantastic views. "
United States
Downer F.
$433 nightly
The price is $470
Apr 6 - Apr 7
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
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 6 - Apr 7
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, (112 reviews)
"Cozy & dog friendly "
United States
Lauren F.
$190 nightly
The price is $201
Apr 12 - Apr 13
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, (85 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
$265 nightly
The price is $295
Apr 6 - Apr 7
Total with taxes and fees
Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
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, (66 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
$246 nightly
The price is $261
Apr 6 - Apr 7
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
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.
$232 nightly
The price is $246
Apr 9 - Apr 10
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown

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, (124 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
$263 nightly
The price is $279
Apr 6 - Apr 7
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Exterior

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Myersville
9.4 out of 10, Exceptional, (111 reviews)
"Great, unique house full of cool antiques! Host was helpful and communicative, highly recommended for a Myersville stay."
United States
Ryan W.
$279 nightly
The price is $296
Apr 7 - Apr 8
Total with taxes and fees
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Dining

Cozy w Fireplace, Fire Pit, Wifi & Pool Access

Cozy w Fireplace, Fire Pit, Wifi & Pool Access
The Woods
9.8 out of 10, Exceptional, (59 reviews)
"The host was very responsive whenever I texted about questions and doing a check in the day of and a check in the day of checkout. The house was beautiful and well maintained and any minor issues I had were quickly addressed. I would definitely stay at this house in the future. "
United States
Paula M.
$367 nightly
The price is $399
Apr 6 - Apr 7
Total with taxes and fees
Cozy w Fireplace, Fire Pit, Wifi & Pool Access
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 7 - Apr 8
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
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.
$222 nightly
The price is $235
Apr 6 - Apr 7
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
$344 nightly
The price is $392
Apr 6 - Apr 7
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Dining

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*
Downtown Frederick
9.0 out of 10, Wonderful, (81 reviews)
"The place was perfect. Location is ideal to walk everywhere."
United States
Anonymous traveler
$213 nightly
The price is $226
Apr 6 - Apr 7
Total with taxes and fees
*Luxury Condo In Downtown Frederick*
Property grounds

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
$140 nightly
The price is $148
Apr 13 - Apr 14
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.6 out of 10, Excellent, (4 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
$255 nightly
The price is $264
Apr 6 - Apr 7
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (36 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
$317 nightly
The price is $353
Apr 6 - Apr 7
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
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, (20 reviews)
"Great view, very secluded"
United States
Matt s.
$339 nightly
The price is $377
Apr 6 - Apr 7
Total with taxes and fees
Cottage w/ Hot Tub and 100-Mile Valley Views!
Terrace/patio

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Sleepy Hollow
8.8 out of 10, Excellent, (29 reviews)
"This is a great property for a quiet and relaxing stay. "
United States
David G.
$314 nightly
The price is $339
Apr 6 - Apr 7
Total with taxes and fees
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Fridge, microwave, oven, stovetop

*Modern Condo In Downtown Frederick*

*Modern Condo In Downtown Frederick*
Downtown Frederick
9.2 out of 10, Wonderful, (86 reviews)
"The location was perfect - walking distance to everything we wanted to do in Frederick. The place was clean and comfortable for 2 couples. "
United States
N. N.
$213 nightly
The price is $226
Apr 9 - Apr 10
Total with taxes and fees
*Modern Condo In Downtown Frederick*
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

Comfort Inn Frederick - Ballenger Creek

Comfort Inn Frederick - Ballenger Creek

10/10 Excellent
"The room was spacious, and the breakfast was a nice perk in the morning. It was more up-to-date than comparable hotels we've stayed in recently."
Chris 1-night trip
Posted 8 hours ago
Comfort Inn Frederick - Ballenger Creek

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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home rental near Shepherdstown offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 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.