Shepherdstown Guest Houses

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Shepherdstown hotels

Guest Houses in Shepherdstown

The Bluebird Suite at Harpers Ferry Guest House

Harpers Ferry WV

$170 nightly

$189 total

Dec 16 - Dec 17

Total with taxes and fees

With a stay at this guesthouse in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy Headquarters.

Free WiFi

Air conditioning

►New! Unique Custom Crafted Train Station Lodge W/ private walking trails

Martinsburg WV

$237 nightly

$264 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Martinsburg, this guesthouse is within a 15-minute drive of A-T Gift Company Farm Winery and James Hite Park.

Free WiFi

Air conditioning

The Goldfinch Suite at Harpers Ferry Guest House

Harpers Ferry WV

$170 nightly

$189 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy Headquarters.

Air conditioning

Parking available

Mountain Retreat • Arcade • Golf • Fire Pit • Trails • Views

Mercersburg PA

With a stay at this guesthouse in Mercersburg, you'll be within a 10-minute walk of Whitetail Ski Resort and Expert's Choice.

Pool

Hot Tub

The Cardinal Suite at Harpers Ferry Guest House

Harpers Ferry WV

$181 nightly

$202 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy Headquarters.

Free WiFi

Air conditioning

The Chickadee Room at Harpers Ferry Guest House

Harpers Ferry WV

$154 nightly

$171 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy Headquarters.

Air conditioning

Parking available

Historic Cottage Retreat-IG Cowboy Pool-Hot Tub

Boonsboro MD

$245 nightly

$260 total

Dec 14 - Dec 15

Total with taxes and fees

When you stay at this guesthouse in Boonsboro, you'll be within a 10-minute drive of Crystal Grottoes Caverns and Greenbrier State Park.

Hot Tub

Pet friendly

Riverview Suite at La Soledad

Harpers Ferry WV

$411 nightly

$458 total

Dec 24 - Dec 25

Total with taxes and fees

With a stay at this guesthouse in Harpers Ferry, you'll be on the waterfront, within a 15-minute drive of Hollywood Casino at Charles Town Races and Woodpecker Woods Wildlife Santuary.

Air conditioning

Parking available

INDULGE - FRESH FLOWERS, MANY AMENITIES

Middletown MD

$155 nightly

$164 total

Dec 28 - Dec 29

Total with taxes and fees

When you stay at this guesthouse in Middletown, you'll be within a 10-minute drive of Orchid Cellar Winery and Willow Oaks Craft Cider and Wine.

Free WiFi

Air conditioning

Stone Leaf Farm Private Nature Retreat with Pool, Waterfalls, Orchards & Gardens

Jefferson MD

When you stay at this guesthouse in Jefferson, you'll be on a river, within a 5-minute drive of Point of Rocks Community Commons Park and Heaters Island.

Pool

Pet friendly

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.