Shepherdstown Holiday Rentals

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Our top choices for Shepherdstown holiday rentals

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful views "
United States
Darryl L.
The price is NZ$807
includes taxes & fees
6 Apr - 7 Apr
Exclusive Wooded Chalet w Magnificent River Views

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (72 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is NZ$235
includes taxes & fees
14 Apr - 15 Apr
❤️ Secluded 1940s Romantic Tiny House on the River

Renovated WV Schoolhouse: History Buffs Heaven!

Renovated WV Schoolhouse: History Buffs Heaven!
3.0 star property
Kearneysville
10.0 out of 10, Exceptional, (3 reviews)
"This was the cutest place to stay! We loved the school house as well as the area. "
United States
Lynn
Renovated WV Schoolhouse: History Buffs Heaven!

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Historic & Cozy ~ Near Antietam Battle & WhiteTail
Hagerstown
10.0 out of 10, Exceptional, (33 reviews)
"We keep coming back to this rental. It’s a great location, the apartment is cozy and it’s always easy to book and use."
United States
Don H.
Historic & Cozy ~ Near Antietam Battle & WhiteTail

Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (46 reviews)
"Prime location for all things in Harpers Ferry!! "
United States
Annette K.
The price is NZ$563
includes taxes & fees
22 Apr - 23 Apr
Enchanting Cottage, walk to Downtown Harpers Ferry

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
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.
The price is NZ$560
includes taxes & fees
5 Apr - 6 Apr
Antietam Creek - Quiet 2 Bedroom Cabin

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (66 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is NZ$446
includes taxes & fees
6 Apr - 7 Apr
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is NZ$724
includes taxes & fees
9 Apr - 10 Apr
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
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.
The price is NZ$425
includes taxes & fees
6 Apr - 7 Apr
Chic, pets, walk to downtown

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"Absolutely amazing place and stay! I could not possibly be more impressed and I look forward to coming back."
United States
Jasmine M.
The price is NZ$674
includes taxes & fees
3 Apr - 4 Apr
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hillside Hideaway in Lowertown Harpers Ferry

Hillside Hideaway in Lowertown Harpers Ferry
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 traveller
The price is NZ$895
includes taxes & fees
7 Apr - 8 Apr
Hillside Hideaway in Lowertown Harpers Ferry

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (42 reviews)
"Loved this home. Host was excellent with A communication. Beautiful setting adjacent to Antietam Battlefield. "
United States
Cbragaw B.
The price is NZ$484
includes taxes & fees
13 Apr - 14 Apr
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
8.6 out of 10, Excellent, (4 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is NZ$488
includes taxes & fees
5 Apr - 6 Apr
2-Bedroom cabin Hot tub Fireplace PS5

Birch Cabin at Hunting Creek Hideaway

Birch Cabin at Hunting Creek Hideaway
Thurmont
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful location. Just what we were looking for."
United States
tony l.
The price is NZ$257
includes taxes & fees
13 Apr - 14 Apr
Birch Cabin at Hunting Creek Hideaway

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is NZ$561
includes taxes & fees
5 Apr - 6 Apr
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
9.8 out of 10, Exceptional, (8 reviews)
"Clean room, spacious intimate setting "
United States
Camille
The price is NZ$793
includes taxes & fees
5 Apr - 6 Apr
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!

Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!
Purcellville
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay while in Purcellville! Super close to everything in town. Clean and smelled great. Easy check in process and the owners are very responsive. Thanks!"
United States
Brian L.
The price is NZ$349
includes taxes & fees
14 Apr - 15 Apr
Cozy Apartment w/ King bed in lovely VA Wine Country; Enough room for up to 6!

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (32 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is NZ$597
includes taxes & fees
22 Apr - 23 Apr
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (28 reviews)
"Clean, great location, friendly owner"
United States
Christian M.
The price is NZ$357
includes taxes & fees
8 Apr - 9 Apr
Cozy, dog-friendly, downtown

Pet-friendly, heart of downtown

Pet-friendly, heart of downtown
Frederick
10.0 out of 10, Exceptional, (8 reviews)
"This was a great property in an excellent location! Communication was great and the whole process was seamless. "
United States
nikki b.
The price is NZ$344
includes taxes & fees
15 Apr - 16 Apr
Pet-friendly, heart of downtown
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 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 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 NZ$235 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?

Exclusive Wooded Chalet w Magnificent River Views: This highly rated holiday home rental in Shepherdstown offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Shepherdstown?

Expedia has 10 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.