Holiday Rentals in Shepherdstown

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Holiday Rentals in Shepherdstown

Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is €137
per night
2 Jun - 3 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, (18)
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is €201
per night
4 Jun - 5 Jun
Cozy Cottage
Welcome to this patch of serenity on the river's edge, to this hideaway.
9.8 out of 10, Exceptional, (57)
"We had a really lovely time at this space, Amy was such a good host, and we hope to return!"
Welcome to this patch of serenity on the river's edge, to this hideaway.
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Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, (20)
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
Fridge, microwave, oven, stovetop
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
9.8 out of 10, Exceptional, (32)
"A diamond in such a remote area, the host has really gone above and beyond to make a relaxing and accommodating stay."
The price is €274
per night
22 May - 23 May
Waterfront Cabin overlooking the Potomac River W/ Hot Tub
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
10.0 out of 10, Exceptional, (28)
"Very nice clean cabin in a very quiet location. enjoyed our stay watching the deer come by everyday and other wildlife."
The price is €311
per night
23 May - 24 May
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
Property grounds
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, (51)
"Beautiful historic toll house. very comfortable and well stocked ..you wont be disappointed"
Antietam Toll House~ an historic waterfront cabin
TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.6 out of 10, Exceptional, (8)
"Beautiful property, quiet, and very spacious. This property had everything we were looking for in a getaway. My family enjoyed our time together here. We did have a power outage and I let Tony know as soon as the power went out. He was quick to respond and even gave updates. Loved the communication from Tony throughout our whole experience. Definitely would stay here again and at another one of his properties."
The price is €282
per night
29 May - 30 May
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (49)
"We really enjoyed our stay! The hot tub, game room, fire pit, and smart TV were all great! It was a beautiful woodsy getaway for sure and it was peaceful."
Hidden Gem in the woods with hot tub
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"Sweet place! We brought out dog, and it felt like a second home - safe, beautiful, and easy."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"It was farther from Harper’s Ferry then I expected. However to location was beautiful."
The price is €209
per night
2 Jun - 3 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (99)
"Very clean and well-kept house!"
The price is €275
per night
27 May - 28 May
Charming "Cream of the Crop" Cape ~❤️of Middletown
Interior
Lake House w/ Pool and King Bed, Fishing - Dogs OK
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay, really nice place we enjoyed seeing the water"
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (92)
"We had a lovely stay in this beautiful Harpers Ferry home. It was so amazing to stay in the historical area and be close and able to walk to all the National Park sites. We were most attracted to that lovely porch and enjoyed our coffee there in the early morning, watching the town come to life. We also liked afternoons reading and napping there and an evening glass of wine after dinner. The kitchen was well stocked with everything we needed, the furniture and beds were very comfortable. We will...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (61)
"Wonderful cabin with all you could need. Fantastic location to many many attractions activities, especially if you enjoy history. Cabin is so cozy and the decorations are real enjoyable and every where you look is something you didn't see before. Host was terrific to work with and helpul. Resetve a visit you will not regret it."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.4 out of 10, Exceptional, (6)
"The hosts received a notice that we had lost heat at the house. We actually did not, but they were out the next morning to check the furnace and brought two space heaters we did not have to use. Really enjoyed our stay."
Charming Home with Yard Near Shenandoah River!
TV, books, stereo, computer monitors
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, (17)
"We had previously visited Frederick last November and had only been able to spend a little bit of our visit in Historic Frederick. We loved staying in historic Frederick and the property was unique, very clean and well laid out. I should have realized was that 'penthouse' in a historic home would mean steps. I am blind in one eye and have poor physical balance so carrying luggage up stairs is challenging. Nonetheless, we loved the layout and amenities of the property. The view from the deck was...
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Property grounds
The Oculus - Huge Cabin with a Hot Tub!
10.0 out of 10, Exceptional, (11)
"This property is so wonderful. Great location. Wonderfully comfortable beds! And very clean! We look forward to coming back!"
The Oculus - Huge Cabin with a Hot Tub!
View from property
Antietam Creek - Quiet 2 Bedroom Cabin
9.4 out of 10, Exceptional, (71)
"Perfect quiet spot to relax and spend quality time! Cabin was as listed and was just what we needed!"
The price is €312
per night
27 May - 28 May
Antietam Creek - Quiet 2 Bedroom Cabin
Property grounds
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, (9)
"The location tucked away on the lake with a dock and kayaks and gravity lounge chairs, fireplace, large dock and gas grill were fabulous."
Rustic Log Cabin with Private Dock on the Lake!
Don't see what you're looking for?
See all available properties in Shepherdstown
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.

Other types of properties in Shepherdstown you may be interested in

Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is €137
includes taxes & fees
2 Jun - 3 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Hilton Garden Inn Frederick
3.0 star property
9.0 out of 10, Wonderful, (1000)
"The check-in service was excellent! unfortunately, there was a problem. The hotel had a main water pipe burst at 3:45am. that resulted in the entire hotel being evacuated. I do want to say the check-in clerk was exceptional in handling this situation. He assured us the hotel would give us a refund if we called Expedia. I was given the info. that Expedia needed to process the refund and it appears that this will be taken care of. Thank-you so much and thank-you (check-in clerk) Art."
The price is €112
includes taxes & fees
9 Jun - 10 Jun
Hilton Garden Inn Frederick
Room, 2 Queen Beds, Non Smoking
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1000)
"Nice and clean. Very good quality-price ratio."
The price is €80
includes taxes & fees
28 May - 29 May
Country Inn & Suites by Radisson, Frederick, MD
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.

Everything you need to know about Shepherdstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shepherdstown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherdstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherdstown holiday rentals we have selected for you start as low as €137 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown holiday 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 holiday.

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 holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shepherdstown has to offer?

Welcome to this patch of serenity on the river's edge, to this hideaway.: This highly rated holiday home rental in Shepherdstown is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Shepherdstown?

Expedia has 9 holiday 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 holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.

Recent reviews of Shepherdstown properties
Expedia verified reviews

The Inn at Charles Town

The Inn at Charles Town

5/5 Excellent
"The Inn was everything we needed. Front Desk Team was very polite and helpful. Shuttle driver was friendly and the shuttle was timely. The breakfast was "continental" but offered many options. I would definitely stay again."
A verified traveller stayed at The Inn at Charles Town
Posted 1 day ago
The Inn at Charles Town