Discover a selection of 300 vacation rentals in Shepherdstown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $89 per night, and cabins and houses are popular options for a stay in Shepherdstown. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Shepherdstown
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

Travel to historic Shepherdstown

The area's history and opera are just a few of the reasons to vacation in 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 vacation or friends trip, 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 vacation rental, you'll want to experience everything that makes Shepherdstown a fun spot to vacation. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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

Transportation 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 center. 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.

How many vacation rentals are available around Shepherdstown?

Our 2021 property listings offer a large selection of 300 vacation rentals around Shepherdstown. From 55 cabin rentals to 233 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.