Choose from 6 vacation rentals located in Shepherdstown, Virginia. Top filters in Shepherdstown include Internet / Wifi, Air conditioner, and Kitchen / Kitchenette. Prices range from $89 to $245 per night. Our most popular vacation rental types near Shepherdstown are Hotel and RV.

Top vacation rentals in Shepherdstown

Front of the house.
5.0
Outstanding(72 Reviews)
House
 in Shepherdstown
BEST LOCATION: Historic Shepherdstown Getaway
8 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our House in Shepherdstown has everything you need for a rejuvenating stay. Treat yourself to BEST LOCATION: Historic Shepherdstown Getaway's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Room
4.9
Outstanding(16 Reviews)
Condo
 in Shepherdstown
Downtown Modern 2BR step from dining and shopping
5 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience vacation in Shepherdstown with our Condo, Downtown Modern 2BR step from dining and shopping. Enjoy amenities such as Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
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Exterior
4.5
Excellent(16 Reviews)
Cottage
 in Shepherdstown
Cozy Cottage
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

This Cottage for $94 in Shepherdstown, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
4.8
Outstanding(8 Reviews)
Farm Stay
 in Shepherdstown
Farmhouse Writer's Retreat in Historic Shepherdstown
6 guests · 3 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Nestled in Shepherdstown, this Farm Stay is perfect for your next vacation. Enjoy Farmhouse Writer's Retreat in Historic Shepherdstown's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Shepherdstown

Shepherdstown travel guide

Let us help you plan your perfect Shepherdstown vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Shepherdstown, and more.

Frequently asked questions

What do I need to know before visiting Shepherdstown, WV?

Before visiting Shepherdstown, WV, it's important to know the following:
  • Shepherdstown is located in West Virginia, just two hours away from Washington, D.C.
  • The town is home to Shepherd University, a liberal arts college.
  • Shepherdstown is considered to be the oldest town in the state of West Virginia.
Shepherdstown is known for its vibrant culture, offering a variety of events and attractions. Visitors should plan to attend the annual July 4th celebration, the Appalachian Festival, and the Taste of Shepherdstown, which showcases local food and art. Additionally, there are many outdoor activities, such as hiking, fishing, and kayaking, available in the area.

What are the must-visit tourist attractions in Shepherdstown, WV?

Shepherdstown, WV is a beautiful town with plenty of tourist attractions to keep visitors busy. Here are four must-visit attractions in Shepherdstown, WV:

  • The Historic Shepherdstown Museum
  • The Morgan's Grove Park
  • The Shepherdstown Visitors Center
  • The Rumsey Monument

The Historic Shepherdstown Museum offers visitors a chance to learn about the town's rich history. Morgan's Grove Park is a great spot for picnics, nature walks, and other outdoor activities. The Shepherdstown Visitors Center provides helpful information about the town and its attractions. Finally, the Rumsey Monument is a great spot to take photos and learn about the town's Civil War history.

How can I get around in Shepherdstown, WV?

You can get around Shepherdstown, WV in the following ways:

  • By car
  • By bike
  • By foot

Additionally, there are a few bike rental shops in town, and the Shepherd University campus has a free shuttle service for students.

Where can I find affordable accommodation in Shepherdstown, WV?

Shepherdstown offers a variety of affordable accommodation options. Here are a few to consider:

  • The Bavarian Inn – located in the heart of Shepherdstown, this hotel offers comfortable rooms at an affordable rate.
  • The Clarion Inn – provides rooms with modern amenities at a great price.
  • The Comfort Inn – offers comfortable rooms and a convenient location.
  • The Towne House Motor Lodge – offers a great value for a clean, comfortable stay.

No matter which option you choose, you'll be sure to find an affordable and comfortable stay in Shepherdstown.

What is the culture like in Shepherdstown, WV?

Shepherdstown, WV is a small town with a big personality. It is a place where people come from all backgrounds, and its culture is vibrant and diverse. Here are five ways that culture is expressed in Shepherdstown:

  • The town celebrates its history with the annual Civil War Living History Encampment held in July.
  • The town is home to a variety of festivals, such as the annual Appalachian Festival and the Shepherdstown Street Fest.
  • The town is known for its excellent restaurants, such as the Yellow Brick Bank and the Press Room.
  • The town hosts a variety of events, such as the Old Time Music Festival and the Shepherdstown Film Festival.
  • The town is home to a variety of unique shops, such as the Lost Dog Coffee Shop and the Shepherdstown Sweet Shop.

Is Shepherdstown, WV safe to travel to?

Shepherdstown, WV is generally a safe place to travel to. Here are some safety tips to follow while visiting:

  • Be aware of your surroundings and trust your instincts.
  • Be aware of local laws and customs.
  • Be sure to lock your doors and windows when you are away from home.

What are the popular shopping destinations in Shepherdstown, WV?

Shepherdstown, WV has many popular shopping destinations for visitors and locals alike. Here are a few of the most popular:

  • Shepherdstown Visitors Center & Gift Shop
  • The Yellow Brick Bank
  • The Shepherdstown Sweet Shop
  • The Town Run Tap House & Community Pub

What are the best neighborhoods to visit in Shepherdstown, WV?

The best neighborhoods to visit in Shepherdstown, WV are:

  • Downtown Shepherdstown
  • Shepherdstown Historic District
  • Morgan's Grove Park

Downtown Shepherdstown is a vibrant and lively area with plenty of shops, restaurants, and bars to explore. Shepherdstown Historic District is a great place to view historic architecture and learn about the area’s past. Morgan's Grove Park is a great place for outdoor activities such as hiking, biking, and picnicking.

Where is Shepherdstown, WV?

Shepherdstown, WV is located in the eastern panhandle of West Virginia, about 78 miles northwest of Washington, DC. It is known as the oldest town in West Virginia, having been established in 1762. Shepherdstown is home to Shepherd University, a liberal arts college founded in 1871.

What are the most popular vacation rental amenities in Shepherdstown, WV?

The most popular vacation rental amenities in Shepherdstown, WV are:

  • Fully equipped kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Cable TV
  • Laundry facilities

Additional popular amenities include a fireplace, hot tub, pet-friendly policies, and outdoor activities such as hiking and biking trails. Vacation rentals in Shepherdstown are also known for their stunning views of the Potomac River, as well as their proximity to historic sites, antique shops, and wineries.

What are the top things to do in Shepherdstown, WV?

Shepherdstown, WV offers a variety of activities for visitors and locals alike. Here are a few of the top things to do in Shepherdstown:

  • Explore the historic downtown area
  • Visit Cress Creek Nature Preserve
  • Take a tour of the historic Entler Hotel
  • Visit one of the many local wineries

No matter what you're looking for, Shepherdstown has something for everyone. Whether you're looking for a fun day out with friends or a peaceful afternoon in nature, Shepherdstown has you covered.

What is the price range for rentals in Shepherdstown?

Vacation rentals in Shepherdstown have a price range between $89-$245. The average price for rentals in Shepherdstown is $171 per night.

What are the most popular vacation rental amenities in Shepherdstown?

  • Internet / Wifi
  • Air conditioner
  • Kitchen / Kitchenette

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