81+ Private Villas and Holiday Rentals in Shepherdstown |
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  2. West Virginia
  3. Martinsburg
  4. Shepherdstown

Shepherdstown Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Shepherdstown

Discover more than 81 vacation rentals available in Shepherdstown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Shepherdstown.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Shepherdstown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Shepherdstown. On average, places to stay near Shepherdstown offer 1159.17 ft², with nightly prices averaging CA $416.

With Casai, finding and comparing holiday rentals in Shepherdstown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Shepherdstown

Type Count
Vacation Homes 43
Cottages 10
Holiday Apartments 9

Use these Quick Filters to Find a Holiday Rental in Shepherdstown

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Shepherdstown.

Weather in Shepherdstown, WV

View the weather forecast for Shepherdstown before booking your Shepherdstown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Shepherdstown, WV

Casai offers a large selection of top attractions around Shepherdstown . Research things to do on your vacation before you visit Shepherdstown.


Shepherd University
Shepherdstown Opera House
Rumsey Steamboat Museum
Shepherdstown Visitors Center
Cress Creek Golf Club
Shepherdstown Museum
Elmwood Cemetery
Rumsey Monument
Morgan's Grove Park
Whitetail Ski Resort
Hollywood Casino at Charles Town Races
Harpers Ferry National Historical Park
Hagerstown Premium Outlets
Catoctin Mountain Park
Hagerstown Speedway
Westview Promenade
Frederick Memorial Hospital
Antietam National Battlefield
Maryland Theater
Francis Scott Key Mall

Other Places to Stay in Shepherdstown, WV


Shepherdstown Opera House 65 Properties
Shepherdstown Museum 65 Properties
Rumsey Steamboat Museum 65 Properties
Shepherdstown Visitors Center 65 Properties
Shepherd University 64 Properties
Elmwood Cemetery 64 Properties
Morgan's Grove Park 62 Properties
Rumsey Monument 60 Properties
Cress Creek Golf Club 54 Properties

Frequently Asked Questions About Shepherdstown?

What are the top holiday rentals in Shepherdstown?

With numerous options available in Shepherdstown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Shepherdstown:

Which holiday homes in Shepherdstown are best for families?

If you're searching for a family-friendly holiday home in Shepherdstown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Shepherdstown:

How many Casai.ca holiday rentals are available in Shepherdstown?

As of 2025, Casai boasts over 81 properties listed in the Shepherdstown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Shepherdstown.


People Also Ask

There are 81 Shepherdstown, WV Holiday Rentals

Recently Booked Holiday Rentals in Shepherdstown