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 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.

Where to stay near Shepherdstown?

Our 2019 accommodation listings offer a large selection of 248 holiday rentals near Shepherdstown. From 86 Cabins to 86 Cottages, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Shepherdstown for a long holiday or a weekend break is on Stayz.

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

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

  • Rumsey Monument: 128 holiday rentals
  • Shepherd University: 127 holiday rentals
  • Cress Creek Golf Club: 126 holiday rentals
  • Shepherdstown Visitors Center: 126 holiday rentals
  • Shepherdstown Opera House: 125 holiday rentals

But there are many other points of interest around Shepherdstown listed on Stayz 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 Cabins in Shepherdstown?

Yes, of course. Stayz offers 86 Cabins in Shepherdstown. Our other popular types of Shepherdstown holiday rentals include:

  • Cottages: 86 holiday houses
  • Houses: 93 holiday houses
  • Bungalows: 86 holiday houses

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

Can I find a holiday accommodation with pool in Shepherdstown?

Yes, you can select your preferred holiday accommodation with pool among our 74 holiday homes with pool available in Shepherdstown. Please use our search bar to access the selection of holiday rentals available.