Book Holiday Homes in Shepherdstown
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Featured Holiday Homes in Shepherdstown

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

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

Modern Country House on the Shenandoah River

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

Gorgeous 1840 Log Cabin- Downtown

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Shepherdstown Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Shepherdstown vacation homes are the perfect way for you to wing it.
Holiday houses in Shepherdstown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Shepherdstown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Shepherdstown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shepherdstown with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Shepherdstown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Shepherdstown Holiday Homes essential information
Accommodation | 309 Holiday Homes |
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Lowest Price | AU$144 |
Highest Price | AU$658 |
Popular accommodation | Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Walk to Harpers Ferry! Dog-friendly. Beautiful Views., Modern Country House on the Shenandoah River , Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC, Gorgeous 1840 Log Cabin- Downtown, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Lake House w/ Pool and King Bed, Fishing - Dogs OK, Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!, Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry |
Top Locations for Holiday Homes in Shepherdstown
More accommodations in Shepherdstown
Top trending hotels in Shepherdstown

Quality Inn Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

Country Inn & Suites by Radisson, Frederick, MD

Hilton Garden Inn Frederick
More ways to explore Shepherdstown
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^Subject to availability and chosen travel dates.