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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is AED 444
AED 813 total
includes taxes & fees
29 Sep - 30 Sep
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
9.6 out of 10, Exceptional, (85 reviews)
"Enjoyed my stay I appreciate the view and Rich. "
United States
Joseph
The price is AED 145
AED 385 total
includes taxes & fees
5 Oct - 6 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A traditional living room with a fireplace, floral-patterned furniture, and a large rug.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is AED 591
AED 1,013 total
includes taxes & fees
28 Sep - 29 Sep
Charming Shepherdstown Home - Walk to Downtown
Smart TV, DVD player, books, video library

4. BEST LOCATION: Historic Shepherdstown Getaway

BEST LOCATION: Historic Shepherdstown Getaway
Shepherdstown
10.0 out of 10, Exceptional, (112 reviews)
"Wonderful host, great location, everything was a expected"
United States
Dave D.
The price is AED 727
AED 1,481 total
includes taxes & fees
28 Sep - 29 Sep
BEST LOCATION: Historic Shepherdstown Getaway
Outdoor dining

5. 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
The price is AED 1,665
AED 2,577 total
includes taxes & fees
14 Oct - 15 Oct
Exclusive Wooded Chalet w Magnificent River Views

6. Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia

Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
Shepherdstown
The price is AED 2,944
AED 3,475 total
includes taxes & fees
14 Oct - 15 Oct
Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
TV, fireplace

7. 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
The price is AED 470
AED 1,443 total
includes taxes & fees
30 Sep - 1 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Room

8. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 966
AED 1,217 total
includes taxes & fees
25 Oct - 26 Oct
Schilling House
Interior

9. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (97 reviews)
"We had a great stay! Everything was clean & well organized. The house was well stocked with everything we need. We would definitely stay here again."
United States
Stephen V.
The price is AED 735
AED 1,207 total
includes taxes & fees
27 Sep - 28 Sep
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

10. 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, (48 reviews)
"Rental was exactly as advertised and in a great location within walking distance of a lot of great spots to check out."
United States
Sarah D.
The price is AED 533
AED 925 total
includes taxes & fees
27 Sep - 28 Sep
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Interior

11. 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.
The price is AED 661
AED 1,716 total
includes taxes & fees
8 Oct - 9 Oct
Antietam Look Out - Incredible Sunset Views!
Property grounds

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (59 reviews)
"Great location. We'll kept up."
United States
Robert
The price is AED 659
AED 1,037 total
includes taxes & fees
1 Oct - 2 Oct
Best location! The Pullman Apt @ historic 1799 Inn
Interior

13. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is AED 776
AED 1,716 total
includes taxes & fees
27 Sep - 28 Sep
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Exterior

14. 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.
The price is AED 424
AED 730 total
includes taxes & fees
28 Sep - 29 Sep
Beautiful, Historic, Hiking, Biking and C&O Canal
Interior

15. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
The price is AED 802
AED 1,356 total
includes taxes & fees
27 Sep - 28 Sep
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
1 bedroom, WiFi, bed sheets

16. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful location. Very peaceful and convenient for everything we wanted to do on our trip. Enjoyed all the deer while sitting outside the cottage reading."
United States
Clinton R.
The Carriage House at Carrot Top Cottage
Interior

17. 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.
The price is AED 396
AED 739 total
includes taxes & fees
28 Sep - 29 Sep
Loft Apt Just off C&O near Harpers Ferry and AT
Terrace/patio

18. 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, (47 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is AED 559
AED 1,142 total
includes taxes & fees
29 Sep - 30 Sep
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
TV, fireplace

19. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our getaway. Clean and comfortable. Close to everything."
United States
Ashlee O.
Cozy Getaway Near History, Hiking & Adventure
Terrace/patio

20. 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, (61 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is AED 511
AED 1,057 total
includes taxes & fees
13 Oct - 14 Oct
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"The whole property was clean from inside out. It smell good overall it was a very good stay."
Nicole 2-night trip
Posted 23 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

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.