Shepherdstown vacation rentals

We found 864 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Shepherdstown that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Shepherdstown

Showing deals for:Nov 21 - Nov 28

Image gallery for Hot Tub, Fire Pit, Game Room, Family Getaway

Exterior of the cabin!
9.6 out of 10 rating
Exceptional
(8 reviews)

Hot Tub, Fire Pit, Game Room, Family Getaway

Berkeley Springs, WV

9% off
Price is CA $342
CA $3,127 total
includes taxes & fees
Hot Tub, Fire Pit, Game Room, Family Getaway

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Find out more about Shepherdstown

Find out more about Shepherdstown

Head to the historic city of Shepherdstown

The area's history and opera are just a few of the reasons to vacation in Shepherdstown. Travelers to this scenic city praise the university setting, riverfront and hiking. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Shepherdstown

Are you hoping to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Shepherdstown has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Big Cork Vineyards (7.6 mi / 12.2 km)
  • Sleepy Hollow Country Club (8.3 mi / 13.4 km)
  • Hollywood Casino at Charles Town Races (9.5 mi / 15.2 km)
  • Locust Hill Golf Course (11.1 mi / 17.8 km)
  • 868 Estate Vineyards (14.2 mi / 22.8 km)
  • Breaux Vineyards (14.4 mi / 23.1 km)

Exploring the natural landscape of Shepherdstown

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Shepherdstown. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Antietam Creek (4.3 mi / 7 km)
  • Chesapeake and Ohio Canal (6.3 mi / 10.2 km)
  • Crystal Grottoes Caverns (8.2 mi / 13.3 km)
  • Greenbrier State Park (12.2 mi / 19.6 km)
  • Shenandoah Lake Beach (15.2 mi / 24.5 km)
  • Morgan's Grove Park (1.1 mi / 1.8 km)

Traveling to and around Shepherdstown

Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), the closest airport, located 10.1 mi (16.3 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 19.4 mi (31.2 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Shepherdstown?
Prices for vacation rentals in Shepherdstown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Shepherdstown to more spacious homes.
Are there any discounts for Shepherdstown vacation house rentals?
You can find great discounts on house rentals in Shepherdstown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Shepherdstown?
In Shepherdstown, a variety of vacation rentals are available, with vacation houses, apartments, cottages, mobile homes, and cabins all featuring prominently—each type being represented by several properties throughout the area. Many of these rentals are situated in charming neighbourhoods near points of interest such as the historic downtown, the picturesque Potomac River, and the nearby Civil War sites.
Are there any family house rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are numerous family-friendly house rentals available, with around 12 options to choose from. This charming town is known for its historic sites and scenic beauty, making it an inviting destination for families. Properties in the area often come with spacious living areas, fully equipped kitchens, and amenities such as outdoor patios or gardens where children can play.
Can I find long-stay vacation rentals in Shepherdstown?
A long-stay vacation rental in Shepherdstown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are several pet-friendly house rentals available for travellers. Many of these properties feature charming amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups with pets.

The town is known for its historic charm and vibrant arts scene, providing a delightful atmosphere for visitors. Nearby, the picturesque C&O Canal National Historical Park offers beautiful trails superb for walking your dog, along with scenic views of the Potomac River. Additionally, the local parks, such as Morgan's Grove Park, are great spots for pets to enjoy some outdoor time.
Are there any remote work vacation rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are several remote work-friendly vacation rentals available, with about 13 options to choose from. This historic town, known for its charming streets and vibrant arts scene, provides an excellent backdrop for those looking to blend work and leisure. Many of the properties come equipped with essential remote work amenities such as dedicated office spaces, comfortable desk chairs, and high-speed Wi-Fi, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shepherdstown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Shepherdstown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Shepherdstown?
In Shepherdstown, popular vacation rentals typically feature essential amenities for a comfortable stay. Most properties include a fully equipped kitchen, allowing travellers to prepare their meals with ease. This is complemented by cookware, dishware, and utensils, making it convenient for those who enjoy cooking. Additionally, rentals often come with a microwave and a refrigerator, further enhancing the self-catering experience. These amenities cater to visitors seeking a cozy feel while exploring the charming town and its nearby attractions.
When is the best time to visit Shepherdstown for a vacation rental?
The best time to book a vacation rental in Shepherdstown is during the peak summer season, which runs from June to August. This vibrant period attracts visitors eager to immerse themselves in the town's rich history and enjoy the warm, inviting weather. With average temperatures in the mid-20s Celsius, it's great for exploring the scenic beauty of the area, wandering along the Potomac River, or attending the lively local events that dot the calendar during these months.

July stands out as the most popular month for travellers, offering an array of outdoor activities and cultural experiences. The town comes alive with festivals, music events, and farmers' markets, creating a delightful atmosphere that truly captures the essence of Shepherdstown. The abundance of nearby hiking trails and picturesque spots makes it easy to appreciate the natural wonders just a stone's throw away.

For those seeking a more budget-friendly option, consider visiting in December. This month allows for a great experience, with the charm of the festive season enveloping the town. Enjoy the twinkling lights and vacation spirit while exploring local shops and cafes in a quieter atmosphere.
How early should I book a Shepherdstown vacation rental?
Book your Shepherdstown vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Shepherdstown?
In Shepherdstown, visitors can engage in a rich tapestry of history and natural beauty. The historic downtown area features charming 18th-century architecture, with local shops and cafes along German Street. Key attractions include the Shepherdstown Museum, which showcases the town's past, and the nearby Rumsey Monument, dedicated to a local hero of the Revolutionary War. Outdoor enthusiasts can explore the scenic banks of the Potomac River, great for kayaking and fishing, as well as the picturesque trails at the nearby C&O Canal National Historical Park.
Can I change or cancel my Shepherdstown home rental booking on Vrbo?
To find Shepherdstown vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Shepherdstown vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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