86+ Vacation Rentals & Holiday Homes in Shepherdstown |
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Shepherdstown Accommodations - Hotels & Rentals

About Shepherdstown Vacation Rentals

Discover More than 86 Incredible Getaway Rentals Available in Shepherdstown. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Shepherdstown.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Shepherdstown, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Shepherdstown. The Average Size of Places to Stay Near Shepherdstown is 1219.85 ft², with Prices Averaging US $314 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Shepherdstown. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Shepherdstown

Type Count
Vacation Homes 47
Holiday Apartments 10
Cottages 10

Use these Quick Filters to Find a Vacation Rental in Shepherdstown

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Shepherdstown with Online Reservations.

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

Activities ShepherdstownGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World ShepherdstownGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


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 hotels, lake houses & vacation rentals in Shepherdstown?

We provide an array of great vacation destinations in Shepherdstown. If you are looking to stay in or around the Shepherdstown area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Shepherdstown:

Which hotel, lake house, or vacation rental in Shepherdstown is best for families?

Searching for a family-friendly getaway in Shepherdstown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Shepherdstown?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 86 in the Shepherdstown area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Shepherdstown.


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