Shepherdstown Vacation Rentals

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Our top choices for Shepherdstown vacation rentals

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
$95 nightly
The price is $105
Mar 9 - Mar 10
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
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 2 - Mar 3
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views

Apartment in Frederick

Pet-friendly, heart of downtown
10.0 out of 10, Exceptional, (8 reviews)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
$173 nightly
The price is $184
Mar 2 - Mar 3
Total with taxes and fees
Pet-friendly, heart of downtown
9.6 out of 10, Exceptional, (111 reviews)
"I’ve stayed here and will absolutely stay again."
United States
Katherine M.
$165 nightly
The price is $175
Mar 4 - Mar 5
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
$144 nightly
The price is $153
Mar 2 - Mar 3
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway

Apartment in Frederick

Cozy, dog-friendly, downtown
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
$181 nightly
The price is $192
Mar 2 - Mar 3
Total with taxes and fees
Cozy, dog-friendly, downtown
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.
$244 nightly
The price is $259
Mar 3 - Mar 4
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
9.8 out of 10, Exceptional, (67 reviews)
"Great stay! We would book again. "
United States
Sam F.
$332 nightly
The price is $369
Mar 5 - Mar 6
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
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.
$321 nightly
The price is $357
Mar 5 - Mar 6
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!

Vacation Home in Downtown Frederick

*Luxury Condo In 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
$247 nightly
The price is $262
Mar 2 - Mar 3
Total with taxes and fees
*Luxury Condo In Downtown Frederick*
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
Mar 4 - Mar 5
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
10.0 out of 10, Exceptional, (7 reviews)
"Host was very responsive before and during my stay. Apartment is beautifully appointed and has all the amenities you need for a great weekend stay!!"
United States
lizbeth g.
$202 nightly
The price is $214
Apr 1 - Apr 2
Total with taxes and fees
Huge 1br apt, baby-friendly, dogs, walkable downtown
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.
$314 nightly
The price is $333
Mar 2 - Mar 3
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
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.
$278 nightly
The price is $299
Mar 9 - Mar 10
Total with taxes and fees
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (122 reviews)
"Great location — right on the Carroll Creek Walk and a stone’s throw from excellent restaurants and nice shops. "
United States
Darby R.
$251 nightly
The price is $266
Mar 23 - Mar 24
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.0 out of 10, Wonderful, (64 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
$297 nightly
The price is $309
Mar 4 - Mar 5
Total with taxes and fees
Cozy cabin w/private hot tub & game room
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, great amenities, comfortable!"
United States
James
$449 nightly
The price is $500
Mar 2 - Mar 3
Total with taxes and fees
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

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.
$216 nightly
The price is $229
Mar 3 - Mar 4
Total with taxes and fees
Chic, pets, walk to downtown
9.8 out of 10, Exceptional, (31 reviews)
"Would come back anytime, very scenic and easy check-in process"
United States
Mark F.
$343 nightly
The price is $382
Mar 3 - Mar 4
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
9.8 out of 10, Exceptional, (65 reviews)
"Beautiful home, quiet and peaceful."
United States
Dina A.
$332 nightly
The price is $369
Mar 5 - Mar 6
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
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

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.

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 Museum and Shepherdstown Opera House, 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.