Discover a selection of 266 vacation rentals in Shepherdstown, WV 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 kitchens and swimming pools. Prices start at $45 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.
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 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, WV?

Our 2020 property listings offer a large selection of 266 vacation rentals around Shepherdstown. From 83 cabin rentals to 101 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Shepherdstown?

None can resist a room with a view. But if you're after views that'll make you feel like you're on cloud nine, you'll need to head for the hills. Vrbo has no less than 94 mountain rentals available. Alternatively, you might be interested in trying a different style of vacation setting. Vrbo has no lack of options, including:

  • 88 rural vacation rentals.
  • 27 water-view vacation rentals.
  • 23 shore-front vacation rentals.

Can I rent a house in Shepherdstown?

Rather than staying in a forgettable, cookie-cutter hotel room this vacation, you could just go for an entire house. You'll feel like you're a part of the neighborhood in no time! There are 99 houses available on Vrbo. Prices begin at $85 per night. If that doesn't suit your posse's taste, we've got a range of different rental options available, such as:

  • Cabin: 57 vacation homes. Prices start from $43 per night.
  • Hotel: 49 vacation homes. Prices start from $45 per night.
  • Cottage: 32 vacation homes. Prices start from $125 per night.

Can I stay in Shepherdstown in a large group?

The recipe for a memorable vacation is catching up with friends and relatives in a fantastic new place. If you'll be hitting the road with a big group, Vrbo has options for you. House vacation homes are the top choice here for big groups of travelers. Our worldwide database presently has 23 available. The vacation properties that can provide for large groups in the area include:

  • If yours is a crew of 6, we offer 116 vacation homes ideal for that size. Book a night from just $40.
  • If you have 8 in your squad, you'll be delighted to hear that there are 68 vacation homes perfect. Prices start at $140 per night.
  • Planning a trip away with a group of 10? We have 56 vacation homes that will suit. Prices start from $200 per night.

You and all your mates will be in good hands when you book your Shepherdstown travels with us!

Where are the cheapest rentals in Shepherdstown?

There are friends, there is family and then there are friends that become family. Rejuvenate the bonds with those who truly matter and organize an economical stay with Vrbo. The Woods is perfect for bargain hunters. And with 16 Vrbo rentals at an average price of $179 a night, you can see why. Sleepy Hollow is another place to check out. We've got 3 rentals here, and the average price is around $212 a night.