Shepherdstown Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Shepherdstown vacation rentals

Dining

Vacation Home in Shepherdstown

Exclusive Wooded Chalet w Magnificent River Views
10.0 out of 10, Exceptional, (16 reviews)
"This property was super nice and the property managers were super awesome and accommodating! "
United States
Construction V.
$433 nightly
The price is $470
Mar 16 - Mar 17
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Exterior

Cabin in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River
9.8 out of 10, Exceptional, (72 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
$122 nightly
The price is $135
Mar 24 - Mar 25
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

Cabin in Shepherdstown

Charming Cabin in the Woods with River Access
9.6 out of 10, Exceptional, (44 reviews)
"The cabin was spotless and Owners had left many thoughtful amenities"
United States
Stephen
$271 nightly
The price is $302
Mar 15 - Mar 16
Total with taxes and fees
Charming Cabin in the Woods with River Access
Apartment (3 Bedrooms) | Front of property

Apartment in Frederick

2 Mi to Dtwn Frederick: Updated Townhome
4.0 star property
$468 nightly
The price is $496
Mar 14 - Mar 15
Total with taxes and fees
2 Mi to Dtwn Frederick: Updated Townhome
Interior

Cabin in The Woods

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
$267 nightly
The price is $277
Mar 17 - Mar 18
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
Interior

Cabin in Keedysville

Antietam Creek - Quiet 2 Bedroom Cabin
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
Mar 16 - Mar 17
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Terrace/patio

Cabin in Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
10.0 out of 10, Exceptional, (19 reviews)
"The house is in a perfect spot to explore downtown Harpers Ferry! So much history within walking distance and so many beautiful homes. "
United States
Anonymous traveler
$398 nightly
The price is $443
Mar 15 - Mar 16
Total with taxes and fees
Hillside Hideaway in Lowertown Harpers Ferry
1 bedroom, premium bedding, down comforters, laptop workspace

Chalet in Mercersburg

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
9.8 out of 10, Exceptional, (7 reviews)
"Clean room, spacious intimate setting "
United States
Camille
$438 nightly
The price is $470
Mar 16 - Mar 17
Total with taxes and fees
Mirror Villas - Modern Retreat with private hot tubs and mountain view
Exterior

Vacation Home in Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
9.6 out of 10, Exceptional, (45 reviews)
"Prime location for all things in Harpers Ferry!! "
United States
Annette K.
$296 nightly
The price is $310
Mar 30 - Mar 31
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
Interior

Chalet in Harpers Ferry

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.2 out of 10, Wonderful, (31 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
$282 nightly
The price is $303
Mar 18 - Mar 19
Total with taxes and fees
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Interior

Cottage in Hamilton

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
9.8 out of 10, Exceptional, (12 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
Mar 15 - Mar 16
Total with taxes and fees
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

Cabin in Clear Spring

Glamping Clear Spring Maryland 3-Cabin Campground
9.8 out of 10, Exceptional, (16 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.
$358 nightly
The price is $398
Mar 15 - Mar 16
Total with taxes and fees
Glamping Clear Spring Maryland 3-Cabin Campground
Fridge, microwave, oven, stovetop

Cottage in Frederick

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
10.0 out of 10, Exceptional, (64 reviews)
"We had a great time. House was very comfortable and location was perfect."
United States
Liz R.
$239 nightly
The price is $253
Mar 23 - Mar 24
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Microwave, oven, stovetop, dishwasher

Vacation Home in Rohrersville

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
10.0 out of 10, Exceptional, (7 reviews)
"The hosts were easy to work with. The house was need and clean! Great experience!"
United States
Chad S.
$400 nightly
The price is $424
Mar 20 - Mar 21
Total with taxes and fees
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Terrace/patio

Cabin in Sleepy Hollow

Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
9.0 out of 10, Wonderful, (28 reviews)
"This is a great property for a quiet and relaxing stay. "
United States
David G.
$266 nightly
The price is $285
Mar 22 - Mar 23
Total with taxes and fees
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi
Exterior

Apartment in Brunswick

Beautiful, Historic, Hiking, Biking and C&O Canal
10.0 out of 10, Exceptional, (23 reviews)
"For visiting Harpers Ferry, location was ideal."
United States
Barbara W.
$189 nightly
The price is $200
Mar 15 - Mar 16
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Interior

Cabin in Bolivar

Minutes to Downtown Harpers Ferry, Hot Tub
9.6 out of 10, Exceptional, (20 reviews)
"Miles within Harper’s Ferry historical site. "
United States
Jeff H.
$338 nightly
The price is $365
Mar 15 - Mar 16
Total with taxes and fees
Minutes to Downtown Harpers Ferry, Hot Tub
Outdoor dining

Vacation Home in Frederick

Chic, pets, walk to downtown
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay. The place has perfect and the location was close to everything downtown. The host was great. Will definitely stay there again."
United States
Patrick H.
$229 nightly
The price is $242
Mar 23 - Mar 24
Total with taxes and fees
Chic, pets, walk to downtown
Exterior detail

Vacation Home in Harpers Ferry

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
9.8 out of 10, Exceptional, (107 reviews)
"Booked this property for my entire extended family for a wedding. It was perfect for the 18 of us with plenty of room for everyone to have their own space to relax. The common areas were also big enough for us all to have a conversation. "
United States
Staci H.
$700 nightly
The price is $779
Mar 27 - Mar 28
Total with taxes and fees
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Interior

Cabin in Keedysville

Antietam Look Out - Incredible Sunset Views!
9.8 out of 10, Exceptional, (35 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
$317 nightly
The price is $353
Mar 17 - Mar 18
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherdstown Hotel Reviews

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

10/10 Excellent
"Driving through the area and needed to stay overnight to take the Amtrak Auro train the next day. I wanted to see the property in person and the area prior to booking. Location was safe, located by a lot Of food options. Now don’t expect the Ritz Carlton, this hotel serves its purpose clean, comfy bed, safe, nice people working there. I have to say you can tell they pay attention when cleaning rooms extremely clean but of course normal wear and tear. The noise of doors shutting and loud people yes you will hear but for the price, location, cleanliness and safe that’s all that matters. "
Macy 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Frederick, MD

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 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.