Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Shepherdstown vacation rentals

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

1. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is AED 444
AED 1,305 total
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A spacious living room with a large window, a wooden coffee table, and a sofa.

2. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 855
AED 1,099 total
includes taxes & fees
15 Nov - 16 Nov
Schilling House
A modern bedroom with a large bed, a view of a forest through floor-to-ceiling windows, and a minimalist design.

3. Mirror Villas - Modern Retreat with private hot tubs and mountain view

Mirror Villas - Modern Retreat with private hot tubs and mountain view
3.5 star property
Mercersburg
10.0 out of 10, Exceptional, (29 reviews)
"Great place to unwind and relax."
United States
Candace
The price is AED 1,527
AED 2,246 total
includes taxes & fees
17 Nov - 18 Nov
Mirror Villas - Modern Retreat with private hot tubs and mountain view
A spacious living room with a fireplace, a television, and a large window with curtains.

4. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
The price is AED 560
AED 998 total
includes taxes & fees
12 Nov - 13 Nov
2-Bedroom cabin Hot tub Fireplace PS5
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shepherdstown Hotel Reviews

A hotel room with a bed, a desk, a chair, a desk lamp, a flat-screen TV, a bathroom with a sink and mirror, and a patterned carpet.
Quality Inn Shepherdstown

Quality Inn Shepherdstown

Quality Inn Shepherdstown
Shepherdstown

10/10 Excellent

Really convenient for my trip to the battlefield.
United States
David
Reviewed November 8, 2026
Quality Inn Shepherdstown

Frequently Asked Questions

Are there vacation rentals in Shepherdstown?

Yes, we have vacation rentals near well known local attractions in Shepherdstown, or you can go with a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in Shepherdstown. Make sure you have time to check out the university setting and gardens during your trip.

What's the top vacation rental in Shepherdstown?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Shepherdstown is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Shepherdstown?

Expedia has 10 vacation rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Opera House and Shepherdstown Museum, whereas Morgan's Grove Park is one spot to enjoy nature. While here, Shepherdstown Visitors Center and Shepherdstown Historic District are other places worth a visit.

What’s a vacation rental in Shepherdstown like?

Vacation rentals are private properties you can stay in for a couple of days or more in Shepherdstown. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.