Shepherdstown Vacation Rentals

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Vacation Rentals in Shepherdstown

Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
$95 nightly
The price is $105
Dec 8 - Dec 9
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Outdoor dining
Exclusive Wooded Chalet w Magnificent River Views

Vacation Home in Shepherdstown

10.0 out of 10, Exceptional, (10)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
$430 nightly
The price is $467
Dec 2 - Dec 3
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Fridge, microwave, oven, stovetop
Cozy, dog-friendly, downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
$184 nightly
The price is $195
Dec 2 - Dec 3
Total with taxes and fees
Cozy, dog-friendly, downtown
Smart TV
Pet-friendly, heart of downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
$184 nightly
The price is $195
Dec 2 - Dec 3
Total with taxes and fees
Pet-friendly, heart of downtown
Fridge, microwave, coffee/tea maker, electric kettle
Cozy Pine Tree Nest

Apartment in Frederick

9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
$160 nightly
The price is $170
Dec 8 - Dec 9
Total with taxes and fees
Cozy Pine Tree Nest
Outdoor spa tub
Aslan's How - Cabin with Valley Views & Hot Tub!

Cabin in Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
$343 nightly
The price is $382
Dec 2 - Dec 3
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!
3 bedrooms, free WiFi, bed sheets
Log Cabin w/ Hot Tub & Waterfront Patio!

Cabin in Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (11)
"Everything was great! We had a lovely stay."
United States
Beth D.
$296 nightly
The price is $329
Dec 4 - Dec 5
Total with taxes and fees
Log Cabin w/ Hot Tub & Waterfront Patio!
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Cottage in Frederick

10.0 out of 10, Exceptional, (62)
"We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. "
United States
Karen B.
$243 nightly
The price is $258
Dec 2 - Dec 3
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Property grounds
Birch Cabin at Hunting Creek Hideaway

Cabin in Thurmont

9.8 out of 10, Exceptional, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
$131 nightly
The price is $138
Dec 2 - Dec 3
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway
Terrace/patio
Charming "Cream of the Crop" Cape ~❤️of Middletown

Vacation Home in Middletown

10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
$236 nightly
The price is $250
Dec 2 - Dec 3
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
Outdoor dining
Chic, pets, walk to downtown

Vacation Home in Frederick

10.0 out of 10, Exceptional, (14)
"Beautiful home with all desired ammenaties and very professional owners"
United States
Lawrence S.
$226 nightly
The price is $240
Dec 2 - Dec 3
Total with taxes and fees
Chic, pets, walk to downtown
Game room
Bring Your Own Boat - Meticulously restored house on the Potomac River

Cottage in Hedgesville

10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
$145 nightly
The price is $161
Dec 2 - Dec 3
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
Property grounds
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cabin in Waynesboro

9.8 out of 10, Exceptional, (89)
"Love it been coming here for a few years now "
United States
Kristina M.
$204 nightly
The price is $225
Dec 2 - Dec 3
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Fridge, microwave, oven, stovetop
*Modern Condo In Downtown Frederick*

Condo in Downtown Frederick

9.4 out of 10, Exceptional, (74)
"Enjoyed the hot tub with a view!"
United States
Matthew M.
$249 nightly
The price is $264
Dec 2 - Dec 3
Total with taxes and fees
*Modern Condo In Downtown Frederick*
Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Vacation Home in Frederick

10.0 out of 10, Exceptional, (34)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
$236 nightly
The price is $250
Dec 2 - Dec 3
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Interior
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cabin in Middletown

9.6 out of 10, Exceptional, (110)
"Beautiful cabin with an adorable mini oven, great TV, creature comforts of robes and throws. Best sleep I’ve ever had in the quiet."
United States
Sharon H.
$181 nightly
The price is $192
Dec 2 - Dec 3
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Fridge, microwave, oven, stovetop
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Vacation Home in Jefferson

9.8 out of 10, Exceptional, (58)
"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"
United States
David F.
$236 nightly
The price is $250
Dec 3 - Dec 4
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Fridge, microwave, oven, stovetop
Peaceful Lakefront Cottage with Mountain Views!

Cottage in Harpers Ferry

9.8 out of 10, Exceptional, (30)
"What a great weekend we had! This cottage had everything you could possibly want for a weekend getaway. "
United States
Elaine H.
$332 nightly
The price is $369
Dec 2 - Dec 3
Total with taxes and fees
Peaceful Lakefront Cottage with Mountain Views!
Interior
Antietam Look Out - Incredible Sunset Views!

Cabin in Keedysville

9.8 out of 10, Exceptional, (33)
"The property was perfect for our family. It was well equipped with all the kitchen necessities. plenty of space, bedrooms, and bathrooms to accommodate 7 adults and a 1 yr old. Great location for seeing sites. "
United States
Barbara B.
$321 nightly
The price is $357
Dec 3 - Dec 4
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Dining
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Cabin in Keedysville

9.8 out of 10, Exceptional, (64)
"Great stay! We would book again. "
United States
Sam F.
$330 nightly
The price is $367
Dec 4 - Dec 5
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

10/10 Excellent
"Rénovation moderne, propre, bon service"
Roger 1-night trip
Posted 11 hours ago
Hampton Inn 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 $105 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 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 Cress Creek Country Club Golf Course 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.