Shepherdstown holiday lettings

We found 866 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in Shepherdstown that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include a pool and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Shepherdstown

Showing deals for:6 Mar - 13 Mar

Image gallery for Majestic Equestrian Estate

Expansive Great Room
10 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

Majestic Equestrian Estate

Dickerson, MD

15% off
Price is £5,902
for 7 nights, 1 room
£843 per night
includes taxes & fees
Majestic Equestrian Estate

Find spaces that suit your style

Why visit Shepherdstown

  • Rich history: Discover the captivating historical sites and museums that showcase Shepherdstown's storied past.
  • Outdoor adventures: Enjoy a range of outdoor activities amidst stunning natural scenery, perfect for adventure enthusiasts.
  • Charming streets: Stroll through delightful streets lined with friendly locals and quaint shops, offering a warm welcome.
  • Family-friendly activities: Engage in various excursions suitable for all ages, ensuring a fun holiday for the whole family.
  • Unique accommodation: Choose from a delightful blend of private homes, cottages, and rustic cabins for a memorable stay.

Popular types of accommodation in Shepherdstown

If you're contemplating a getaway to Shepherdstown, you’ll be pleased to know we offer a delightful range of accommodation options. Popular choices include houses, charming cottages, and rustic cabins, ensuring you find the perfect setting for your stay. Whether you're searching for Shepherdstown house rentals, apartments, or cabin retreats, our platform provides transparent information to help you make an informed decision for a memorable holiday.

  • Houses: The top choice for holidaymakers in Shepherdstown, offering spacious and comfortable living for families and groups.
  • Cabins: A charming option for those seeking a rustic retreat, perfect for enjoying the surrounding nature.
  • Cottages: Quaint and cosy, these delightful accommodations provide a homely atmosphere for visitors.
  • Apartments: Ideal for a self-catering experience, these modern spaces cater to various needs and preferences.
  • Chalets: Scenic and unique, chalets offer a distinctive stay amidst picturesque surroundings.**

Top attractions in and around Shepherdstown

Shepherdstown is an ideal destination for those seeking outdoor adventures and stunning scenery, with a wealth of historic sites, visitor centres, and museums to explore. This charming town caters to a variety of travellers, whether you're after cultural experiences or family-friendly activities, ensuring a memorable holiday filled with rich history and natural beauty.

  • Antietam National Battlefield: A poignant historic site, located 2.5km from Shepherdstown, it commemorates the bloodiest single-day battle in American history. Visitors can explore well-preserved landscapes, insightful exhibits, and engaging walking trails that bring the Civil War to life.
  • Shepherd University: Nestled within Shepherdstown, this vibrant modern university blends academic excellence with city vibes. It's an ideal spot to enjoy cultural events, art exhibitions, and the lively atmosphere of student life.
  • Shepherdstown Visitors Center: Situated in the heart of Shepherdstown, this centre serves as a gateway to adventure. With resources for outdoor activities and family-friendly excursions, it’s perfect for planning your exploration of the scenic surroundings.

Things to do recommended for couples

For a romantic getaway in Shepherdstown, indulge in wine tasting at Big Cork Vineyards, bask in luxury at Sleepy Hollow Country Club, or unwind with a couple’s treatment at Vivo Day Spa. Each experience offers a unique blend of charm and relaxation, perfect for couples.

Things to do recommended for families

Families visiting Shepherdstown can explore the scenic C&O Canal National Historical Park, enjoy a delightful day at the local parks, or discover the fascinating history at the Shepherdstown Museum. The charming town offers a perfect blend of outdoor adventure and cultural experiences for all ages.

Things to do recommended for groups

Groups visiting Shepherdstown can enjoy a round of golf at Cress Creek Golf Club, indulge in shopping at Hagerstown Premium Outlets, and experience thrilling motorsports at Summit Point Motorsports Park, perfect for those seeking sports and adventure.

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

If you’re travelling with a group, family, or pets, or if you’re in search of extended stays, be sure to use the appropriate filters to meet your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Shepherdstown with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can refine your search for all of these options and more on Vrbo.
  • Traveling to Shepherdstown with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Shepherdstown: For many, a family holiday isn’t truly enjoyable without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations 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 holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to consider including features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Shepherdstown

Your visit to Shepherdstown, West Virginia, promises a delightful blend of history, adventure, and stunning scenery. Explore the charming streets of this historic town, where friendly locals welcome you. Venture into nearby neighbourhoods and cities, each offering unique excursions and family-friendly activities. Whether you’re seeking a serene getaway or an action-packed outdoor experience, Shepherdstown and its surrounding areas are sure to create lasting memories on your holiday.

  • Harpers Ferry: Nestled 5.0km from Shepherdstown, Harpers Ferry is a picturesque town that beckons adventurers and nature lovers alike. This charming locale is set at the confluence of the Potomac and Shenandoah rivers, offering stunning scenery and ample outdoor activities. Visitors can explore the Harpers Ferry National Historical Park, which is rich in Civil War history, or indulge in thrilling pursuits such as hiking along the Appalachian Trail or skiing in the nearby recreational areas. The town's natural beauty, with its rolling hills and serene lake, makes it a perfect spot for those seeking both adventure and relaxation.
  • Charles Town: Located a mere 6.2km from Shepherdstown, Charles Town is a vibrant city that combines romance with adventure. Known for its exciting racetrack, the Charles Town Races, visitors can enjoy thrilling horse racing events. The city's recreational areas and shopping mall provide a delightful urban experience, while the nearby national park invites exploration of its scenic trails. Charles Town's charming downtown area offers a selection of boutiques and eateries, making it an ideal destination for couples looking to enjoy a romantic getaway or families seeking adventure.
  • Martinsburg: Situated 5.6km from Shepherdstown, Martinsburg is a lively city that offers a blend of outdoor fun and cultural experiences. With access to shopping centres and golf courses, it caters to a variety of interests. The area is surrounded by beautiful landscapes, including lakes and national parks, perfect for leisurely strolls or energetic hikes. History enthusiasts will appreciate the historic sites throughout Martinsburg, adding a cultural dimension to your visit. Whether you're seeking an active day outdoors or a leisurely shopping experience, Martinsburg has something for everyone.

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 simple

Are you eager to save money on your upcoming adventure? It might be worth considering flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for planning your next adventure, allowing you to easily create new trips, resume previous ones, or manage your travel arrangements. You can view the properties you’ve saved or booked, neatly organised under Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the historical city of Shepherdstown

The area's history and opera are just some of the reasons to come on holiday to Shepherdstown. Travellers to this scenic city praise the university setting, riverfront and hiking. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Shepherdstown

Are you searching for top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Shepherdstown a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Big Cork Vineyards (7.6 mi / 12.2 km)
  • Sleepy Hollow Country Club (8.3 mi / 13.4 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)
  • Maryland National Golf Club (15.4 mi / 24.7 km)

Exploring the natural landscape of Shepherdstown

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Shepherdstown is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Killiansburg Cave (2 mi / 3.3 km)

Travelling 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 centre. If you can't find a flight that works for your travel itinerary, 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 when booking a holiday rental?
When considering a holiday rental in Shepherdstown, West Virginia, the most appealing area to stay is the historic downtown district. This charming neighbourhood is rich in character and offers a delightful mix of quaint shops, restaurants, and galleries. Staying here places you within easy walking distance of the iconic Shepherd University, known for its beautiful campus and vibrant cultural events. Additionally, the nearby Antietam National Battlefield provides a fascinating glimpse into American history, making it a must-visit attraction for those interested in the Civil War.
How much does it cost to rent a holiday home in Shepherdstown?
Prices for holiday 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 holiday 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 holiday rental accomodation in Shepherdstown?
In Shepherdstown, a variety of holiday rental options are available, with several holiday houses, apartments, cottages, mobile homes, and cabins scattered throughout the area. Many of these rentals are situated in charming neighbourhoods close to the historic downtown, where visitors can explore local shops, restaurants, and the scenic Potomac River. Most holiday houses and cottages offer fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation, making them ideal for families or groups. The cabins provide a more rustic experience, often featuring amenities like fireplaces and proximity to nature trails.
Are there any family house rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are numerous family-friendly house rentals available, with around twelve options to choose from. This charming town is known for its historic character and picturesque surroundings, making it an appealing destination for families.

Many of the properties feature spacious living areas, well-equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore. Visitors can also expect amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.
Can I find long-stay holiday rentals in Shepherdstown?
A long-stay holiday 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, making it a welcoming destination for travellers with pets. The town's charming historic district offers a variety of holiday homes that often feature amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas, superb for families or groups. Many properties provide private gardens or yards, allowing pets to enjoy the outdoors while you relax.
Are there any remote work holiday rentals in Shepherdstown?
In Shepherdstown, West Virginia, there are several remote work-friendly holiday rentals available, with around 13 options for those looking to blend work and leisure. This charming town, known for its historic charm and scenic views along the Potomac River, offers accommodations that cater to the needs of remote workers. Properties typically come equipped with essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shepherdstown holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
The best time to visit Shepherdstown for a holiday rental is during the peak season from June to August, when the vibrant charm of this historic town truly comes alive. With warm temperatures averaging in the mid to high 20s Celsius, outdoor activities flourish, making it an ideal period for sightseeing, exploring the picturesque streets, and enjoying various local festivals.

July stands out as the most popular month, drawing visitors eager to immerse themselves in the lively atmosphere. This month is filled with opportunities to partake in outdoor events, from farmers' markets to music festivals, offering a rich taste of local culture and community spirit.

For those looking to save while still enjoying the beauty of Shepherdstown, consider visiting in December. This month often brings a festive charm as the town lights up for the holidays, providing a great experience with fewer crowds. The crisp winter air is great for leisurely strolls along the historic buildings and the nearby Potomac River, allowing you to enjoy the serene beauty of the season.
How early should I book a Shepherdstown holiday rental?
Book your Shepherdstown holiday 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 holiday 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 enjoy a blend of historical charm and natural beauty. The town is home to the Shepherd University campus, where the beautiful campus grounds and various cultural events attract many. The historic district features quaint shops, art galleries, and local eateries that showcase the town's vibrant community spirit.
Can I change or cancel my Shepherdstown home rental booking on Vrbo?
To find Shepherdstown holiday 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 cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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