Book Holiday Homes in Shepherdstown

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Featured Holiday Homes in Shepherdstown

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

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

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Potomac River and within a 5-minute drive of Chesapeake and Ohio Canal.
Opens in a new windowRiverside cottage, minutes from historic Harpers Ferry! Private river access!
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV
The price is AU$611 per night from 8 Jan to 9 Jan
AU$611
8 Jan - 9 Jan 2026
includes taxes & fees
Located in Charles Town, this vacation home is on a river, within a 15-minute drive of Shenandoah River and Shannondale Springs Wildlife Management Area.
Opens in a new windowTerra Alta - Incredible River Views and Hot Tub!
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

Frederick MD
The price is AU$466 per night from 11 Jan to 12 Jan
AU$466
11 Jan - 12 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 4 minutes by foot from The Delaplaine Arts ...
Opens in a new windowRETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Shannondale Springs Wildlife Management Area and within a 5-minute drive of ...
Opens in a new windowCozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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

Harpers Ferry WV
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Bolivar Community Park.
Opens in a new windowLarge Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

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

Harpers Ferry WV
The price is AU$941 per night from 26 Dec to 27 Dec
AU$941
26 Dec - 27 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is on a river, within a 5-minute drive of Shenandoah River and Virginius Island.
Opens in a new windowHot Tub, Campfire Ring, Convenient Location, Large Groups!!
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Harpers Ferry WV
The price is AU$720 per night from 28 Dec to 29 Dec
AU$720
28 Dec - 29 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Shannondale Springs Wildlife Management ...
Opens in a new windowCharming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry WV
The price is AU$594 per night from 12 Jan to 13 Jan
AU$594
12 Jan - 13 Jan 2026
includes taxes & fees
With a stay at this vacation home in Harpers Ferry, you'll be within a 5-minute walk of Harpers Ferry Children's Park and Storer College Campus.
Opens in a new windowHistoric Queen Anne Family Home w Modern Comforts
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be within a 5-minute walk of Storer College Campus and Appalachian Trail Conservancy ...
Opens in a new windowFamily-friendly, thoughtfully modernized, historic home in Harpers Ferry.
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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.

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
7 Holiday Homes
Lowest Price
AU$102
Highest Price
AU$941
Popular accommodation
Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Terra Alta - Incredible River Views and Hot Tub!, RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Historic Queen Anne Family Home w Modern Comforts, Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Top trending hotels in Shepherdstown

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
Fully refundable
The price is AU$102 per night from 1 Jan to 2 Jan
AU$102
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Quality Inn Shepherdstown in Shepherdstown, you'll be within a 10-minute walk of Maddex Square and Shepherd University.
Opens in a new windowQuality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is AU$160 per night from 5 Jan to 6 Jan
AU$160
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Shepherdstown, this cabin is on the waterfront, a 1-minute drive from Potomac River and 5 minutes from Shepherdstown Visitors Center.
Opens in a new window❤️ Secluded 1940s Romantic Tiny House on the River
Hampton Inn Martinsburg

Hampton Inn Martinsburg

2.5 out of 5
975 Foxcroft Ave Martinsburg WV
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 1 Jan to 2 Jan
AU$145
1 Jan - 2 Jan 2026
includes taxes & fees
Located in Martinsburg, Hampton Inn Martinsburg is in a rural location, within a 5-minute drive of Wurzburg Dog Park and Tuscarora Creek Historic District.
Opens in a new windowHampton Inn Martinsburg
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Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
7226 Corporate Ct Frederick MD
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 27 Dec to 28 Dec
AU$146
27 Dec - 28 Dec
includes taxes & fees
When you stay at Hilton Garden Inn Frederick in Frederick, you'll be in a shopping district, within a 15-minute walk of Westview Promenade and Regal ...
Opens in a new windowHilton Garden Inn Frederick
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See all available properties in Shepherdstown
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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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^Subject to availability and chosen travel dates.