Shepherdstown Cottages

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Cottages in Shepherdstown

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Frederick MD

$254 nightly

$269 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

With a stay at this cottage in Frederick, you'll be within a 5-minute walk of Baker Park and Frederick Memorial Hospital.

Kitchen

Pet friendly

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Purcellville VA

This cottage is 17.6 mi (28.4 km) from Hollywood Casino at Charles Town Races and 0.3 mi (0.5 km) from Franklin Park.

Kitchen

Washer

Carrot Top Cottage surrounded by National Park

Harpers Ferry WV

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

Kitchen

Air conditioning

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Berkeley Springs WV

$371 nightly

$413 total

Dec 13 - Dec 14

Total with taxes and fees

When you stay at this cottage in Berkeley Springs, you'll be in the mountains and steps from Sleepy Creek Wildlife Management Area.

Kitchen

Washer

Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry WV

$327 nightly

$364 total

Dec 16 - Dec 17

Total with taxes and fees

With a stay at this cottage in Harpers Ferry, you'll be on the waterfront, just steps from Shannondale Springs Wildlife Management Area and a 3-minute drive from Shenandoah Lake Beach.

Hot Tub

Kitchen

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Purcellville VA

This cottage is 17.6 mi (28.4 km) from Hollywood Casino at Charles Town Races and 0.3 mi (0.5 km) from Franklin Park.

Kitchen

Washer

C&O Canal Potomac River Cottage

Sharpsburg MD

With a stay at this cottage in Sharpsburg, you'll be on a river, just a 1-minute walk from Chesapeake and Ohio Canal and 5 minutes by foot from Potomac River.

Kitchen

Washer

Hilltop @ Shiloh Summ

Leesburg VA

With a stay at this cottage in Leesburg, you'll be on the waterfront, just a 1-minute walk from Catoctin Valley and 6 minutes by foot from Springdale Regional Park.

Kitchen

Washer

Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry WV

$307 nightly

$342 total

Dec 17 - Dec 18

Total with taxes and fees

Located in Harpers Ferry, this cottage is in the mountains, within a 5-minute drive of Shannondale Springs Wildlife Management Area and Shenandoah Lake Beach.

Hot Tub

Kitchen

Rustic Cottage near the Potomac River

Knoxville MD

Located in Knoxville, this cottage is in the mountains, a 5-minute walk from Catoctin Valley and within a 5-minute drive of Chesapeake and Ohio Canal.

Kitchen

Washer

Modern Country Cottage in Wine Country

Paeonian Springs VA

With a stay at this cottage in Paeonian Springs, you'll be in the mountains, just a 1-minute walk from Catoctin Valley and 7 minutes by foot from Hunters Run Wine Tasting Barn.

Kitchen

Washer

RIVERKEEPER INN, Waterfront Property on the Potomac River

Harper's Ferry WV

With a stay at this cottage in Harpers Ferry, you'll be on the waterfront, just steps from Potomac River and a 1-minute drive from Chesapeake and Ohio Canal.

Kitchen

Washer

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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.