A street lined with brick buildings, including a bank and a restaurant.

Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Shepherdstown vacation rentals

Dining

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
$197 nightly
The price is $219
Sep 6 - Sep 7
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
Exterior

2. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (83 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
$120 nightly
The price is $133
Sep 14 - Sep 15
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
Dining

3. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
$445 nightly
The price is $485
Sep 7 - Sep 8
Total with taxes and fees
Exclusive Wooded Chalet w Magnificent River Views
Exterior

4. Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (210 reviews)
"Great place, pet friendly. "
United States
Doug P.
$165 nightly
The price is $175
Sep 7 - Sep 8
Total with taxes and fees
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

5. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (53 reviews)
"Loved the place and area."
United States
Steve R.
$301 nightly
The price is $335
Sep 10 - Sep 11
Total with taxes and fees
Charming Cabin in the Woods with River Access
Living area

6. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (75 reviews)
"Beautiful cabin in the forest especially in the evening when the fire flies out and the sun sets."
United States
Jared
$346 nightly
The price is $385
Sep 10 - Sep 11
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior

7. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$331 nightly
The price is $369
Sep 22 - Sep 23
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
Interior

8. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
$310 nightly
The price is $329
Sep 7 - Sep 8
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
Room

9. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
$195 nightly
The price is $217
Sep 10 - Sep 11
Total with taxes and fees
The Carriage House at Carrot Top Cottage
Interior

10. Loft Apt Just off C&O near Harpers Ferry and AT

Loft Apt Just off C&O near Harpers Ferry and AT
Brunswick
10.0 out of 10, Exceptional, (21 reviews)
"The place was nice and cozy"
United States
Andrew E.
$189 nightly
The price is $200
Sep 4 - Sep 5
Total with taxes and fees
Loft Apt Just off C&O near Harpers Ferry and AT
Interior

11. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (45 reviews)
"We loved our stay, very cozy "
United States
Scot G.
$210 nightly
The price is $233
Sep 7 - Sep 8
Total with taxes and fees
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Property grounds

12. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.4 out of 10, Exceptional, (57 reviews)
"Great location. We'll kept up."
United States
Robert
$253 nightly
The price is $282
Sep 7 - Sep 8
Total with taxes and fees
Best location! The Pullman Apt @ historic 1799 Inn
Terrace/patio

13. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (44 reviews)
"Great place to stay for the weekend."
United States
Bea G.
$272 nightly
The price is $303
Sep 13 - Sep 14
Total with taxes and fees
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Exterior

14. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (55 reviews)
"Area was great, host was super helpful and communicative "
United States
Riya L.
$366 nightly
The price is $385
Sep 13 - Sep 14
Total with taxes and fees
Enchanting Cottage, walk to Downtown Harpers Ferry
Exterior

15. Schilling House

Schilling House
3.0 star property
Bolivar
$310 nightly
The price is $331
Oct 4 - Oct 5
Total with taxes and fees
Schilling House
Terrace/patio

16. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Bolivar
10.0 out of 10, Exceptional, (58 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
$294 nightly
The price is $328
Sep 13 - Sep 14
Total with taxes and fees
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Exterior

17. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
$188 nightly
The price is $199
Sep 7 - Sep 8
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
Interior

18. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Just what I needed. Great place."
United States
Shannon W.
$145 nightly
The price is $161
Oct 1 - Oct 2
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River
Room

19. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Great spot"
China
Clara
$277 nightly
The price is $309
Sep 7 - Sep 8
Total with taxes and fees
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Interior

20. Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (35 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
$297 nightly
The price is $320
Sep 14 - Sep 15
Total with taxes and fees
Forest chalet w/ hot tub & BBQ grill
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

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

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

10/10 Excellent
"If you are anywhere on the East Coast and looking for a nice getaway or time to reset and just chill...you should definitely make this a spot to visit. I thoroughly enjoyed my time and wished I could have extended my stay. The mirror cabins were gorgeous. The attention to detail was lovely. My partner and I loved having the ability to barbecue, dip in the hot tub, and next time I'm booking the room with the sauna! My fiance, he loved looking at all Miami Vice episodes on the projector! You definitely want to make a trip over to this part of Pennsylvania and oddly enough, you're close to the Maryland and West Virginia borders, so you can make it a 3 state trip almost in one day! We enjoyed our time and will definitely will be back. Note: there is a lot of gravel to ride up on so make sure if you are not riding a 4wd or awd that your tires are solid! And like another guest said just be careful walking around the cabin in your knickers (or not) with the lights on at night! Make your booking now!"
Renee 3-night trip
Posted 1 hour ago
Mirror Villas - Modern Retreat with private hot tubs and mountain view

Find out more about Shepherdstown

Everything you need to know about Shepherdstown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherdstown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shepherdstown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherdstown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shepherdstown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $133 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shepherdstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherdstown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherdstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.: This vacation home rental near Shepherdstown is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Shepherdstown?

Expedia has 9 vacation rentals for your stay in Shepherdstown.

What’s there to see and do in Shepherdstown?

Cultural attractions include Shepherdstown Museum and Shepherdstown Opera House, 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.