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

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

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

Harpers Ferry
When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood ...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

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

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be a 2-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino ...
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Modern Country House on the Shenandoah River

Modern Country House on the Shenandoah River

Charles Town
When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.
Modern Country House on the Shenandoah River
Save an average of 15% on thousands of hotels when you're signed in
Charming Historic Victorian 4 bedroom guesthouse in  Rohrersville with WiFi, AC

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

Rohrersville
The price is AU$658 per night from 9 Sept to 10 Sept
AU$658
9 Sept - 10 Sept
includes taxes & fees
With a stay at this vacation home in Rohrersville, you'll be within a 5-minute drive of Big Cork Vineyards and South Mountain State Park.
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Gorgeous 1840 Log Cabin- Downtown

Gorgeous 1840 Log Cabin- Downtown

Frederick
With a stay at this vacation home, you'll be centrally located in Frederick, just a 4-minute walk from Frederick Memorial Hospital and 9 minutes by foot from ...
Gorgeous 1840 Log Cabin- Downtown
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
When you stay at this vacation home in Harpers Ferry, you'll be in the mountains, within a 10-minute drive of Harpers Ferry National Historical Park and Hollywood ...
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Lake House w/ Pool and King Bed, Fishing - Dogs OK

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

Hedgesville
Located in Hedgesville, this vacation home is on the waterfront, within a 15-minute drive of Potomac River and Rooney Park.
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

Harpers Ferry
The price is AU$524 per night from 25 Aug to 26 Aug
AU$524
25 Aug - 26 Aug
includes taxes & fees
Located in Harpers Ferry, this vacation home is in the mountains, within a 15-minute drive of Shannondale Springs Wildlife Management Area and Shenandoah Lake ...
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2 out of 5
Harpers Ferry
The price is AU$485 per night from 19 Aug to 20 Aug
AU$485
19 Aug - 20 Aug
includes taxes & fees
With a stay at this vacation home in Harpers Ferry, you'll be a 2-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino ...
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Don't see what you're looking for?
See all available properties in Shepherdstown
View all properties
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
309 Holiday Homes
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 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$165 per night from 7 Sept to 8 Sept
AU$165
7 Sept - 8 Sept
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.
Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is AU$220 per night from 14 Sept to 15 Sept
AU$220
14 Sept - 15 Sept
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.
❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is AU$144 per night from 24 Aug to 25 Aug
AU$144
24 Aug - 25 Aug
includes taxes & fees
A stay at Country Inn & Suites by Radisson, Frederick, MD places you in the heart of Frederick, just a 5-minute walk from Francis Scott Key Mall and within a ...
Country Inn & Suites by Radisson, Frederick, MD
Save an average of 15% on thousands of hotels when you're signed in
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$186 per night from 31 Aug to 1 Sept
AU$186
31 Aug - 1 Sept
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 ...
Hilton Garden Inn Frederick
Don't see what you're looking for?
See all available properties in Shepherdstown
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.