A street lined with brick buildings, including a bank and a restaurant.

Shepherdstown cottage rentals

We found 48 cottage rentals — enter your dates for availability

Explore Shepherdstown cottage rentals

Image of Quaint Mini Cottage in Shepherdstown - Walking Distance

Premier Host

Quaint Mini Cottage in Shepherdstown - Walking Distance

Sleeps 6 · 1 bedroom · 1 bathroom

Image of RIVERKEEPER INN, Waterfront Property on the Potomac River

Premier Host

RIVERKEEPER INN, Waterfront Property on the Potomac River

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Bring Your Own Boat - Meticulously restored house on the Potomac River

Premier Host

Bring Your Own Boat - Meticulously restored house on the Potomac River

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Mountain Top View Spacious Family Cottage Walking Distance from Appalachian Trl

Mountain Top View Spacious Family Cottage Walking Distance from Appalachian Trl

Sleeps 8 · 2 bedrooms · 1 bathroom

Image of C&O Canal Potomac River Cottage

Premier Host

C&O Canal Potomac River Cottage

Sleeps 5 · 3 bedrooms · 1 bathroom

Image of Cozy Custom-built Cottage in pleasant Point of Rocks with WiFi and AC

Premier Host

Cozy Custom-built Cottage in pleasant Point of Rocks with WiFi and AC

Sleeps 4 · 1 bedroom · 1 bathroom

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