Shepherdstown Holiday Rentals

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Holiday Rentals in Shepherdstown

Our top choices for Shepherdstown holiday rentals

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is AU$220
includes taxes & fees
28 Sept - 29 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

Quaint Mini Cottage in Shepherdstown - Walking Distance

8.0 out of 10, Very good, (3)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Quaint Mini Cottage in Shepherdstown - Walking Distance

Welcome to this patch of serenity on the river's edge, to this hideaway.

10.0 out of 10, Exceptional, (63)
"Enjoyed our stay!!"
Welcome to this patch of serenity on the river's edge, to this hideaway.

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (42)
"The pictures for this cabin don't reflect how roomy and spacious this place is! It is a very clean, comfortable and quiet retreat. My wife and I had a fantastic stay and would not hesitate to book this place again if we are in the area.Thanks Patty and Bill for allowing us to stay at this wonderful place."
Private, light filled retreat space... with your own pickleball court!

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (126)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (128)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (114)
"We LOVED our stay at Surrey Cabin! Quaint, clean, quiet, and the property is breathtaking! The bed was super comfortable and we had everything we needed. We will definitely be coming back! "
Countryside Cabin with Mountain Views near Surreybrooke Gardens

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (31)
"Very nice rest time…"
The price is AU$451
includes taxes & fees
28 Sept - 29 Sept
Charming Cabin in the Woods with River Access

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

9.8 out of 10, Exceptional, (18)
"We had a great time exploring the region from Spleepy Hollow. The hot tub after a long hike is always great!"
The price is AU$388
includes taxes & fees
2 Sept - 3 Sept
Spacious w/Hot Tub, Fire Pit, Deck, Grill and WiFi

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (56)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is AU$574
includes taxes & fees
4 Sept - 5 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (64)
"We had a great time exploring Harper’s Ferry and loved having this as our home base!"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Enchanting Cottage, walk to Downtown Harpers Ferry

9.6 out of 10, Exceptional, (41)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
The price is AU$480
includes taxes & fees
3 Sept - 4 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is AU$505
includes taxes & fees
7 Sept - 8 Sept
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (82)
"Outstanding property was just what the doctor ordered for a rejuvenating time of R&R. Clean and comfortable, all of the amenities—including the hot tub— made for a lovely stay. "
Hidden Gem in the woods with hot tub

Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

10.0 out of 10, Exceptional, (64)
"Great home with many amenities and beautiful views "
Luxurious Mountaintop Chalet / Cabin in 'The Woods Golf Resort':Access Amenities

Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

9.8 out of 10, Exceptional, (68)
"This little cabin was absolutely wonderful. The nicest amenities and very clean. Had everything we needed for a short weekend getaway. I especially loved the hot tub and the indoor massage chair! We come to this area once a year-will definitely stay here again. "
The price is AU$462
includes taxes & fees
4 Sept - 5 Sept
Waterfront Cabin overlooking the Potomac River W/ Hot Tub, firepit, pavilion

Modern w/Fire Pit, Deck, Grill & Hot Tub

9.0 out of 10, Wonderful, (10)
"Perfect size and location for a quiet getaway to really relax, and the check-ins before, during and after our stay made us feel so welcome!"
The price is AU$409
includes taxes & fees
1 Sept - 2 Sept
Modern w/Fire Pit, Deck, Grill & Hot Tub

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (23)
"The lake house property was clean, comfortable and was an excellent location. We enjoyed the proximity to Gettysburg, Harper’s Ferry, Cacapon State Park and the C and O Towpath bike trail and museum."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is AU$633
includes taxes & fees
3 Sept - 4 Sept
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
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

Find out more about Shepherdstown

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, 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 favourite 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 depend 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 AU$220 per night. Entering your travel dates in the search wizard might find you 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?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Shepherdstown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Shepherdstown?

Expedia has 8 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.