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)
Transport

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.

Where to stay around Shepherdstown?

Our 2019 accommodation listings offer a large selection of 241 holiday lettings near Shepherdstown. From 79 Houses to 86 Cabins, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Shepherdstown is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Shepherdstown?

HomeAway offers a large selection of holiday accommodations near great places in Shepherdstown. From HomeAway travellers, the most popular points of interest to stay near are:

  • Rumsey Monument: 113 holiday lettings
  • Shepherd University: 115 holiday lettings
  • Cress Creek Golf Club: 110 holiday lettings
  • Shepherdstown Visitors Center: 114 holiday lettings
  • Shepherdstown Opera House: 114 holiday lettings

But there are many other points of interest around Shepherdstown listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Shepherdstown?

Yes, of course. HomeAway offers 79 Houses in Shepherdstown. Our other popular types of Shepherdstown holiday rentals include:

  • Cabins: 86 self catering accommodations
  • Cottages: 86 self catering accommodations
  • Bungalows: 86 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Farmhouses and more.

Can I find a holiday accommodation with pool in Shepherdstown?

Yes, you can select your preferred holiday accommodation with pool among our 80 holiday homes with pool available in Shepherdstown. Please use our search bar to access the selection of holiday rentals available.