Discover Your Perfect Shepherdstown Vacation Homes

Best Vacation Homes in Shepherdstown

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10.0 (203 Reviews)
Bed & Breakfast
Antietam Overlook Farm
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
9.9 (7 Reviews)
Bed & Breakfast
Jacob Rohrbach Inn
  • Air Conditioner
  • Parking
  • View
View Availability
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Shepherdstown Luxury Rentals

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Shepherdstown Pet Friendly Vacation Rentals

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Shepherdstown Large Vacation Homes

See More Family Vacation Rentals in Shepherdstown on FVR

Why Choose Rent By Owner for your Shepherdstown Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Shepherdstown

When should you plan your Vacation Rentals stay?

Understanding the best time to visit can help you make the most of your stay in this charming area, ensuring you enjoy its unique atmosphere and attractions during the ideal season.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you can enjoy warm weather and vibrant local events, making it an excellent time to explore the area's natural beauty and cultural activities.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This season offers mild temperatures and stunning foliage, ideal for outdoor activities and soaking in the scenic views of the region.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

With cooler temperatures and quieter surroundings, winter provides a peaceful retreat while still offering cozy accommodations nearby.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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Mid to Late Summer (July to August)

While it's typically warm, this off-peak period sees fewer visitors, which can lead to a more relaxed experience when exploring here.

Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F

Weekly Weather Forecast for Shepherdstown

How to Book Your Shepherdstown Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Shepherdstown

More Top-Rated Vacation Rentals in Shepherdstown Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor space with a barbecue grill for cookouts amidst the scenic surroundings.
  • Relax in a furnished patio or deck, perfect for soaking up the natural beauty of the area.
  • Take advantage of spacious yards ideal for outdoor activities and family gatherings.
  • Make the most of outdoor dining areas to savor meals under the open sky.
  • Benefit from access to nearby hiking trails and scenic overlooks directly from your rental.
  • Utilize outdoor fire pits for cozy evenings and storytelling beneath the stars.
  • Stay active with available outdoor sports amenities like badminton or croquet, common in the region's rentals.

Top Attractions Around Shepherdstown

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities and historic sites that showcase the charm and natural beauty of this destination, making it an ideal choice for your next getaway.

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Family Activities

  • Historic Shepherdstown Walking Tour: Discover the charming streets and rich history of this destination while exploring well-preserved landmarks perfect for family outings.
  • Shepherdstown Visitor Center & Civil War Museum: Engage with interactive exhibits that bring the area's history to life for visitors of all ages, making it an educational experience for the whole family.
  • The Potomac River Waterfront Park: Enjoy scenic views and outdoor activities such as picnicking and leisurely strolls along the river, ideal for family bonding in this region.
  • Local Art and Farmers Markets: Browse handcrafted goods and fresh local produce, providing a fun and authentic taste of the area's vibrant community atmosphere.
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Adult Activities

  • Historical Walking Tours: Discover the rich history and charming architecture of the area through guided or self-guided walking tours.
  • Wineries and Breweries: Enjoy tastings and tours at local wineries and breweries, experiencing the region’s vibrant craft beverage scene.
  • Antique Shopping: Browse a variety of antique shops to find unique collectibles and enjoy the area's nostalgic charm.
  • Art Galleries and Studios: Visit local art galleries and studios to appreciate the region’s creative expression and maybe find a special piece for your collection.

Other Places to Stay in Shepherdstown, WV

Shepherdstown Opera House
Shepherdstown Opera House Vacation Rentals
Shepherdstown Museum
Shepherdstown Museum Vacation Rentals
Rumsey Steamboat Museum
Rumsey Steamboat Museum Vacation Rentals
Shepherdstown Visitors Center
Shepherdstown Visitors Center Vacation Rentals
Shepherd University
Shepherd University Vacation Rentals
Elmwood Cemetery
Elmwood Cemetery Vacation Rentals
Morgan's Grove Park
Morgan's Grove Park Vacation Rentals
Rumsey Monument
Rumsey Monument Vacation Rentals
Cress Creek Golf Club
Cress Creek Golf Club Vacation Rentals
More Places to Stay Near Shepherdstown

Shepherdstown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Sample the region’s traditional dishes at charming eateries to fully immerse yourself in the local culture.
  • Visit Historic Sites: Take time to discover the area’s rich history by exploring prominent landmarks and heritage sites nearby.
  • Plan Outdoor Activities: Make the most of the natural beauty with outdoor adventures like hiking or biking along scenic trails.
  • Discover Unique Shops: Stroll through local stores and markets to find handcrafted goods and souvenirs that capture the essence of here.

Transportation Options

  • Shepherdstown Transit System: This local bus service offers convenient and affordable transportation within the area, making it easy for you to explore this charming destination.
  • Amtrak Railway Stations: For longer journeys, nearby Amtrak stations provide reliable train options to and from this region, connecting you seamlessly to major cities.
  • Rental Car Services: Numerous rental car agencies operate here, giving you the flexibility to explore the region at your own pace during your stay.
  • Taxi and Rideshare Options: Taxis and rideshare services are readily available in this destination, providing quick and comfortable transportation around the area.

Local Customs Options

  • Shepherdstown's Annual Civil War Reenactments: Engaging in this region’s historical reenactments offers an authentic glimpse into its rich past and local traditions.
  • The Shepherdstown Pottery Festival: Participating in or observing this event allows you to experience the region’s vibrant craft heritage firsthand.
  • The German Christmas Market: During the holiday season, locals embrace this festive tradition by showcasing regional crafts and seasonal treats that add to the area's charm.
  • Downtown Farmers Market: Visiting the area’s local farmers market provides a taste of the region’s agricultural roots and fresh, locally sourced produce.

Frequently Asked Questions About Shepherdstown?

1. What are the top vacation rentals in Shepherdstown?

There are a lot of options in Shepherdstown. If you plan on staying in the Shepherdstown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Shepherdstown:

2. Which vacation homes in Shepherdstown are best for families?

If you are looking for a family-friendly vacation home in Shepherdstown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Shepherdstown:

3. How many Rentbyowner vacation rentals are available in Shepherdstown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 81 in the Shepherdstown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Shepherdstown. 

4. What is the cancellation policy for vacation rentals in Shepherdstown, West Virginia?

Cancellation policies vary depending on the property listing. To understand the specific terms and any potential fees, please review the individual property’s cancellation details or contact the host directly before confirming your reservation.

5. How do I find the best vacation rental deals in Shepherdstown?

To secure the best deals, use filters and sorting options to compare prices, amenities, and reviews on the listing platform. Additionally, booking during off-peak times or selecting last-minute offers can help you find more affordable options in this scenic area.

6. Are there any specific check-in or check-out procedures I should be aware of?

Check-in and check-out instructions are provided in each listing. These may include key collection methods or entry codes. It's recommended to read these details carefully or reach out to the host for clarification prior to your arrival to ensure a smooth check-in process.

7. Is it possible to modify or extend my stay at a vacation rental here?

Modifications or extensions to your reservation are subject to the availability of the property and the terms set by the host. Contact the property owner or manager directly through the listing platform to discuss your plans and confirm if changes can be accommodated.

8. What amenities are typically included with vacation rentals in the region?

Most vacation rentals in this area offer essential amenities such as Wi-Fi, kitchen facilities, parking, and heating or air conditioning. For specific features like outdoor spaces or special equipment, review the property listing details or contact the host before booking.