Shepherdstown vacation rentals

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Discover a selection of 9 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:May 22 - May 29

Image gallery for Lake House w/ Pool and King Bed, Fishing - Dogs OK

Property grounds
9.4 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)

Lake House w/ Pool and King Bed, Fishing - Dogs OK

Hedgesville

8% off
Price is $281
$1,965 for 7 nights
All fees included
Lake House w/ Pool and King Bed, Fishing - Dogs OK

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Find out more about Shepherdstown

Why visit Shepherdstown

  • Historic Exploration: Discover Shepherdstown's rich history through its historic sites and charming German Street.
  • Outdoor Adventures: Enjoy stunning natural scenery with ample opportunities for hiking, biking, and outdoor activities.
  • Family-Friendly Atmosphere: Experience the welcoming vibe created by friendly locals, perfect for families and groups.
  • Unique Shopping and Dining: Explore unique shops and inviting cafes that showcase local culture and cuisine.
  • Diverse Accommodation: Choose from a variety of cozy vacation rentals, including cabins and charming cottages.

Popular types of accommodation in Shepherdstown

Discover the charm of Shepherdstown with a variety of vacation rentals to suit your needs. From cozy houses and inviting cabins to charming cottages, there's something for everyone. Whether you're searching for shepherdstown apartments or spacious rental properties, our platform offers numerous options, including bedroom rentals in Shepherdstown and apartment rentals in West Virginia. Dive into your perfect getaway today.

  • Houses: The top choice for visitors to Shepherdstown, these homes offer a spacious and personalized experience, perfect for families or groups.
  • Cabins: A popular option for those seeking a rustic getaway, these cabins immerse you in nature while providing cozy accommodations.
  • Cottages: Ideal for a quaint and charming stay, cottages offer a warm atmosphere for couples or small families.
  • Apartments: A convenient choice, apartments provide all the necessary amenities for a comfortable and independent stay.
  • Chalets: These mountain-style homes offer a unique blend of comfort and scenic views, perfect for a relaxing retreat.**

Top attractions in and around Shepherdstown

Shepherdstown, West Virginia, is a perfect destination for outdoor and adventure enthusiasts, showcasing stunning scenery and rich history. Visitors can explore historic sites, urban parks, and the local visitor center, making it ideal for those seeking cultural experiences and family-friendly activities. Whether you're traveling solo, with family, or friends, Shepherdstown offers a delightful blend of nature and culture that will enhance your vacation experience.

  • Harpers Ferry National Historical Park: Located 8 miles from Shepherdstown, this historic site offers a rich tapestry of American history, stunning views, and outdoor activities. Explore the confluence of the Potomac and Shenandoah rivers, hike scenic trails, and delve into the area's Civil War significance.
  • Shepherd University: Situated in the heart of Shepherdstown, this modern university blends academic excellence with vibrant city vibes. Stroll through its picturesque campus, enjoy cultural events, and experience local student life.
  • Shepherdstown Opera House: A charming venue in Shepherdstown, the Opera House hosts a variety of performances, from live music to theatrical productions. It's an ideal spot for entertainment, romance, and immersing yourself in the local arts scene.

Things to do recommended for couples

For a romantic getaway in Shepherdstown, visit Big Cork Vineyards for a delightful wine tasting, unwind at Sleepy Hollow Country Club for a touch of luxury, and indulge in relaxation at Vivo Day Spa. Each spot offers a unique atmosphere perfect for couples.

Things to do recommended for families

Families will love exploring the historic C&O Canal National Historical Park, where they can hike or bike the scenic trails. Visit the Shepherdstown Museum for a glimpse into local history, or enjoy a fun day at the nearby Potomac River for some outdoor adventures.

Things to do recommended for groups

Groups visiting Shepherdstown can enjoy a round of golf at Cress Creek Golf Club or the Cress Creek Country Club Golf Course for a sporty outdoor experience. For shopping enthusiasts, the Hagerstown Premium Outlets, located 13 miles away, offers a vibrant atmosphere ideal for families and friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Shepherdstown

If you're traveling with a group, your family, bringing along pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Shepherdstown with a group: Take into account how many bedrooms you'll require, along with features like a full kitchen or outdoor area for gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Shepherdstown with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, you should think about how close you are to family-friendly attractions.
  • Taking your pets with you to Shepherdstown: For many families, a vacation isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Shepherdstown: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Shepherdstown

Shepherdstown, West Virginia, is a charming destination perfect for outdoor enthusiasts and history buffs alike. Explore the picturesque German Street, lined with unique shops and inviting cafes. Nearby historic sites offer a glimpse into the town's rich past, while friendly locals create a warm, family-friendly atmosphere. Whether you're seeking adventure in the stunning scenery or a relaxing getaway, Shepherdstown promises a memorable experience filled with cultural excursions and scenic landscapes.

  • Harpers Ferry: Nestled just 8 miles from Shepherdstown, Harpers Ferry is a charming town steeped in history and natural beauty. Known for its stunning outdoor experiences, visitors can explore the Harpers Ferry National Historical Park, where the confluence of the Potomac and Shenandoah Rivers offers breathtaking scenery. Adventure seekers can enjoy activities like hiking, kayaking, and skiing at nearby resorts. The area's rich history, highlighted by its role in the Civil War, makes it a fascinating destination for history buffs and nature lovers alike.
  • Martinsburg: Located 9 miles from Shepherdstown, Martinsburg is a vibrant city that combines outdoor adventures with urban convenience. Visitors can explore lush parks and recreational areas, or indulge in retail therapy at the local shopping malls. Martinsburg is also home to picturesque historic sites and the serene surroundings of local lakes. Whether you're teeing off at a nearby golf course or enjoying a leisurely stroll through the city's historic downtown, Martinsburg offers a delightful mix of adventure and relaxation.
  • Charles Town: Just 10 miles away from Shepherdstown, Charles Town is known for its romantic charm and exciting city-themed experiences. This lively city features a variety of attractions, including the Charles Town Races & Slots, where visitors can enjoy thrilling motor racing. Shopping enthusiasts will appreciate the local mall, while outdoor lovers can explore the scenic beauty of nearby national parks. With its dynamic atmosphere and blend of adventure and leisure, Charles Town is an ideal spot for a memorable getaway.

Best time to go to Shepherdstown

If you're planning a trip to Shepherdstown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnyModerately LowSlightly Low
February34.3°F (1.3°C)Light RainMostly SunnyAverageSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyAverageSlightly Low
April52.9°F (11.6°C)Light RainMostly SunnyAverageAverage
May62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
June71.2°F (21.8°C)Light RainMostly SunnyModerately HighAverage
July76.5°F (24.7°C)Light RainMostly SunnyModerately HighSlightly High
August74.3°F (23.5°C)Light RainMostly SunnyModerately HighSlightly High
September67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
October56.1°F (13.4°C)Light RainMostly SunnyAverageAverage
November43.7°F (6.5°C)Light RainMostly SunnyModerately LowSlightly High
December36.7°F (2.6°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that meets your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the total booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your travels effortlessly. It provides a convenient area where you can start new trip ideas, refine your existing plans, or manage your bookings. You’ll find your saved and booked properties neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • 868 Estate Vineyards (14.2 mi / 22.8 km)
  • Breaux Vineyards (14.4 mi / 23.1 km)
  • Musket Ridge Golf Course (14.4 mi / 23.2 km)
  • Maryland National Golf Club (15.4 mi / 24.7 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:

  • 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)
  • Poor House Farm Park (12.7 mi / 20.5 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

What is the best area to stay in Shepherdstown, West Virginia, United States of America when booking a vacation rental?
When looking for the best area to stay in Shepherdstown, West Virginia, consider the charming historic district. This neighborhood offers a delightful blend of quaint architecture and vibrant local culture, making it an ideal spot for vacation rentals. You'll find a variety of properties, from cozy cottages to larger homes, all within easy walking distance to local attractions.

One of the highlights of this area is the picturesque C&O Canal National Historical Park, superb for outdoor enthusiasts who enjoy hiking or biking along the scenic trails. Additionally, the Shepherdstown Opera House serves as a cultural hub, hosting a range of performances and events that showcase local talent. Staying in the historic district not only provides access to these attractions but also allows you to immerse yourself in the town's rich history and welcoming community atmosphere.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 cater to different preferences, with several options available including vacation houses, cottages, cabins, apartments, and mobile homes. Many of these accommodations are situated in charming neighborhoods near the historic downtown area, allowing easy access to local attractions such as the Shepherd University campus, the Potomac River, and the picturesque C&O Canal. Travelers can expect amenities like fully equipped kitchens, cozy living spaces, and outdoor areas for relaxation. Cabins and cottages often provide a rustic atmosphere, while apartments offer a more urban feel.
Are there any family house rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are some available family-friendly house rentals, with around ten options to choose from. The charming town is located along the Potomac River and is known for its historic downtown, quaint shops, and vibrant arts scene, making it an excellent spot for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to enjoy.

Visitors will appreciate amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. Additionally, the nearby C&O Canal National Historical Park provides opportunities for hiking and biking along the scenic towpath, while the Shepherdstown Library and local parks offer enriching activities for all ages.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Shepherdstown?
In Shepherdstown, West Virginia, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can roam freely. The charming historic district of Shepherdstown offers easy access to local shops, restaurants, and scenic views of the Potomac River, making it a delightful spot for both visitors and their furry companions.

For pet owners, nearby parks and trails provide excellent opportunities for outdoor activities. The C&O Canal National Historical Park, just a short drive away, features picturesque hiking and biking trails along the river, great for leisurely strolls with pets. Additionally, the area is known for its welcoming atmosphere and pet-friendly establishments, enhancing the overall experience for those traveling with animals.
Are there any remote work vacation rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are several remote work vacation rentals available, totaling around 10 options. This charming town, known for its historic architecture and vibrant arts scene, provides a conducive environment for remote work. Many rentals come equipped with essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable living areas, allowing travelers to maintain productivity while enjoying their stay.

The town's location along the Potomac River offers opportunities for outdoor activities, making it easy to take breaks and recharge. Local coffee shops and eateries also provide excellent spots for casual meetings or a change of scenery. 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 travelers 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 rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals with ease. Many properties feature decks or patios, providing outdoor spaces to relax and enjoy the natural surroundings. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, rentals often come with porches or lanais, great for enjoying a morning coffee or evening tea. Coffee and tea makers are also standard in these accommodations, ensuring guests can savor their favorite brews during their stay.
When is the best time to visit Shepherdstown for a vacation rental?
The best time to visit Shepherdstown for a vacation rental is during the peak season from June to August, particularly in July. This vibrant period draws visitors eager to experience the charming small-town atmosphere while enjoying the warm weather and a variety of outdoor activities. The lush greenery and scenic views of the Potomac River provide a picturesque backdrop for exploring the historic sites and engaging in leisurely strolls through the quaint downtown area.

July is especially popular, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit, making it comfortable for outdoor adventures such as hiking, biking, and kayaking. The lively summer events, including local festivals and art shows, add to the excitement, allowing travelers to immerse themselves in the rich culture of Shepherdstown.

If you're looking for a more budget-friendly option, consider visiting in December. While this month falls outside the bustling summer season, it offers a unique winter charm, with the opportunity to enjoy cozy holiday festivities and a quieter pace. The town's historic buildings are beautifully adorned for the season, providing a lovely setting for those who appreciate a more relaxed atmosphere.

Ultimately, your choice of when to visit Shepherdstown will depend on whether you prefer the lively summer energy or the tranquil beauty of winter.
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, West Virginia, United States of America?
In Shepherdstown, visitors can explore a range of attractions that showcase the town's rich history and natural beauty. The historic downtown area features charming boutiques, art galleries, and restaurants housed in 18th-century buildings, making it a delightful place to stroll and shop. For history enthusiasts, the Shepherdstown Museum offers insight into the town's past, including its Civil War significance.

Outdoor lovers can enjoy the scenic beauty of the nearby C&O Canal National Historical Park, which provides opportunities for hiking, biking, and enjoying the Potomac River views. Additionally, the nearby Antietam National Battlefield is a must-visit for those interested in American history, offering a chance to reflect on the pivotal Civil War battle that took place there.

Furthermore, the Shepherd University campus adds a vibrant setting to the town and often hosts cultural events, including concerts and theater productions, contributing to the local arts scene.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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