Shepherdstown Guest Houses

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Guest Houses in Shepherdstown

INDULGE - FRESH FLOWERS, MANY AMENITIES

$100

per night

May 14 - May 15

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

Walk to everything from this historic home in Harpers Ferry!

When you stay at this guesthouse in Harpers Ferry, you'll be on the waterfront, a 1-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino at Charles Town Races.

Free WiFi

Air conditioning

Private lake within 1.5 hours of DC and Baltimore!!!

With a stay at this guesthouse in Clear Spring, you'll be within a 15-minute drive of Knob Hall Winery and Mercersburg Academy.

Air conditioning

Guest House at 1796 Historic Farm in Wine Country

Located in Lovettsville, this guesthouse is in the mountains, a 1-minute drive from Catoctin Valley and 7 minutes from Lovettsville Historical Society and Museum.

Free WiFi

Air conditioning

Step Into A Fairy Tale At This Lavender Farm Guesthouse in Harpers Ferry, WV

When you stay at this guesthouse in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

Free WiFi

Air conditioning

Walk to everything from this historic home in Harpers Ferry!

With a stay at this guesthouse, you'll be centrally located in Harpers Ferry, a 1-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino at Charles Town Races.

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

When you stay at this guesthouse in Martinsburg, you'll be 6 minutes by car from A-T Gift Company Farm Winery.

Free WiFi

Air conditioning

On Whitetail Mtn! Ski & Stay-Hottub, Bathtub, Fire

With a stay at this apartment in Mercersburg, you'll be just steps from Expert's Choice and Sidewinder.

Grove Guest House

5936 Elmer Derr Road, Frederick, MD

Located in Frederick, Grove Guest House is in a rural location, within a 10-minute drive of Frederik Golf Club and Westview Promenade.

Pool

Pet friendly

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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.