Shepherdstown Holiday Homes from £208: Search Holiday Homes in Shepherdstown

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

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Our top choices for Shepherdstown holiday homes

A living room with two leather sofas, a coffee table, and a brick wall.

1. Charming Shepherdstown Home - Walk to Downtown

Shepherdstown

includes taxes & fees

8 Nov - 9 Nov

A deck with green chairs and a fire pit, surrounded by a house and trees.

2. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

Knoxville

Kenzie S.

includes taxes & fees

22 Nov - 23 Nov

A spacious kitchen with modern appliances, a dining area with a large table, and a living room with a sofa and a fireplace.

3. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Harpers Ferry

claire r.

includes taxes & fees

3 Nov - 4 Nov

KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

4. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Sharpsburg

Laura D.

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

5. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Bolivar

Delaine F.

includes taxes & fees

17 Nov - 18 Nov

An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

6. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

Bolivar

Kevin

includes taxes & fees

2 Nov - 3 Nov

A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

7. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Martinsburg

Helen F.

includes taxes & fees

13 Nov - 14 Nov

A wooden staircase with black railings leading to a landing with a door and windows.

8. New, Contemporary House in Historic Harpers Ferry

Harpers Ferry

Erin J.

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a large window, a wooden coffee table, and a sofa.

9. Schilling House

Bolivar

includes taxes & fees

1 Nov - 2 Nov

A wooden cabin with a patio area, outdoor seating, and a fire pit.

10. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Boonsboro

A D.

includes taxes & fees

2 Nov - 3 Nov

A four-poster canopy bed with a view of a cityscape through the window.

11. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Harpers Ferry

Ashley B.

includes taxes & fees

11 Nov - 12 Nov

A two-story house with a porch, green shutters, and a red roof.

12. Enchanting Cottage, walk to Downtown Harpers Ferry

Harpers Ferry

Brett D.

includes taxes & fees

4 Nov - 5 Nov

A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

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

Rohrersville

Kimberly C.

includes taxes & fees

9 Nov - 10 Nov

A hammock on a grassy area with a view of a river and forested hills.

14. La Soledad Lavender Farm on the Potomac

Harpers Ferry

Michel R.

includes taxes & fees

28 Nov - 29 Nov

A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

15. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Harpers Ferry

Katrina

includes taxes & fees

9 Nov - 10 Nov

A hallway with a staircase, a fireplace, and a kitchen area in the background.

16. Cozy Getaway Near History, Hiking & Adventure

Bolivar

Ashlee O.

includes taxes & fees

29 Nov - 30 Nov

A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

17. Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry

Jenny H.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a view of a forested landscape and a sunset.

18. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

Harpers Ferry

"Beautiful setting and a well and thoughtfully appointed home. An aside but helpful tip is that there are not any nearby convenience stores if you forget a little something, so come prepared. The space is comfortable and fun and the view is fantastic, the location is convenient for a lot of local attractions and activities, but we also would have been content to just hang at the house! A very relaxing vibe. We would definitely stay again, and would hopefully share with friends and family, the...

Lori

includes taxes & fees

4 Nov - 5 Nov