Book Holiday Homes in Shepherdstown
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Shepherdstown

*Luxury Condo In Downtown Frederick*

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

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

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

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Modern Country House on the Shenandoah River

*In The Heart Of Antietam*

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
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 | 299 Holiday Homes |
---|---|
Lowest Price | AU$135 |
Highest Price | AU$522 |
Popular accommodation | *Luxury Condo In Downtown Frederick*, Walk to Harpers Ferry! Dog-friendly. Beautiful Views., Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, Modern Country House on the Shenandoah River , *In The Heart Of Antietam* , RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex |
Top Locations for Holiday Homes in Shepherdstown
More accommodations in Shepherdstown
Top trending hotels in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

Charming Cabin in the Woods with River Access

Graycliff Hall: Riverfront Estate w/ Heli Pad, Private Chef, Hot Tub

Country Inn & Suites by Radisson, Frederick, MD
More ways to explore Shepherdstown
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.