Discover a selection of 303 holiday rentals in Shepherdstown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 80 per night, and cabins and cottages are popular options for a stay in Shepherdstown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Shepherdstown
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Destination guide

Travel to historical Shepherdstown

The area's history and opera are just some of the reasons to come on holiday to Shepherdstown. Well known for its university setting, riverfront and hiking, this scenic city won't disappoint. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities

Activities and attractions in and around Shepherdstown

Are you hoping to discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Shepherdstown a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Cress Creek Golf Club (0.5 mi / 0.8 km)
  • Sleepy Hollow Country Club (8.8 mi / 14.2 km)
  • Locust Hill Golf Course (11.4 mi / 18.4 km)
  • Notaviva Vineyards (13.2 mi / 21.2 km)
  • Musket Ridge Golf Course (14.6 mi / 23.4 km)
  • Breaux Vineyards (15 mi / 24.1 km)
How to get there

Transport options to and around Shepherdstown

Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), the closest airport, located 9.9 mi (15.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Hagerstown, MD (HGR-Hagerstown Regional), which is 18.9 mi (30.4 km) away.

Can I find a vacation rental around Shepherdstown?

Yes, our 2021 property listings offer a large selection of 303 vacation rentals near Shepherdstown. From 55 cabins to 52 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Shepherdstown for a holiday or a weekend are on Vrbo.