Shepherdstown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Shepherdstown vacation rentals

House (3 Bedrooms) | Interior

Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is ￥14,804
￥56,457 total
includes taxes & fees
Jun 6 - Jun 7
Walk to Stores: Home in Historic Shepherdstown!
Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (75 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is ￥10,745
￥21,649 total
includes taxes & fees
Jun 3 - Jun 4
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia
Shepherdstown
The price is ￥16,313
￥21,641 total
includes taxes & fees
Jun 1 - Jun 2
"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (126 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is ￥15,759
￥41,339 total
includes taxes & fees
May 25 - May 26
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Exterior

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (6 reviews)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
The price is ￥21,012
￥39,315 total
includes taxes & fees
May 25 - May 26
Historic Getaway near C&O Canal, hiking and biking
Dining

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (89 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is ￥26,615
￥57,435 total
includes taxes & fees
May 26 - May 27
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (115 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is ￥11,939
￥31,553 total
includes taxes & fees
May 25 - May 26
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Property grounds

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Waynesboro
9.8 out of 10, Exceptional, (101 reviews)
"Had a wonderful time!"
United States
Jesse K.
The price is ￥16,555
￥38,159 total
includes taxes & fees
May 25 - May 26
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Fridge, microwave, oven, stovetop

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (68 reviews)
"Great kitchen, very comfortable beds. Well air conditioned."
United States
Whitney C.
The price is ￥18,481
￥41,357 total
includes taxes & fees
May 26 - May 27
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 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.
The price is ￥31,836
￥52,644 total
includes taxes & fees
May 31 - Jun 1
Antietam Creek - Quiet 2 Bedroom Cabin
Smart TV, fireplace

Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (68 reviews)
"Very quiet cabin. Nicely situated between Charles Town and Harper’s Ferry. "
United States
Kelly R.
The price is ￥15,918
￥57,279 total
includes taxes & fees
May 26 - May 27
Blue Ridge Getaway - Sunset Views, A.T. Access
Interior

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is ￥30,146
￥52,205 total
includes taxes & fees
May 26 - May 27
Forest chalet w/ hot tub & BBQ grill
Exterior

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, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is ￥23,081
￥27,840 total
includes taxes & fees
May 25 - May 26
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Outdoor spa tub

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (22 reviews)
"Great view, very secluded"
United States
Matt s.
The price is ￥15,918
￥60,581 total
includes taxes & fees
May 27 - May 28
Cottage w/ Hot Tub and 100-Mile Valley Views!
Smart TV, fireplace

Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (37 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is ￥15,918
￥60,339 total
includes taxes & fees
May 27 - May 28
Secluded Cabin a Stone's Throw From the A.T.!
Exterior

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is ￥14,326
￥39,145 total
includes taxes & fees
May 28 - May 29
Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (44 reviews)
"Loved the place and area."
United States
Steve R.
The price is ￥30,617
￥53,736 total
includes taxes & fees
May 25 - May 26
Charming Cabin in the Woods with River Access
TV, fireplace

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, (67 reviews)
"Great home "
United States
January D.
The price is ￥18,921
￥63,026 total
includes taxes & fees
Jun 1 - Jun 2
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior

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

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.8 out of 10, Exceptional, (11 reviews)
"Our stay was amazing and we really enjoyed ourselves. The place was perfect and quiet and peaceful! We will be booking with them again! "
United States
Kyndal B.
The price is ￥15,741
￥29,905 total
includes taxes & fees
Jun 1 - Jun 2
Bring Your Own Boat - Meticulously restored house on the Potomac River
Outdoor dining

3BR cabin w/ hot tub & game room

3BR cabin w/ hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is ￥31,056
￥57,532 total
includes taxes & fees
Jun 9 - Jun 10
3BR cabin w/ hot tub & game room
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

The Plaza Inn & Suites

The Plaza Inn & Suites

2/10 Terrible
"Nothing was unique and I liked nothing about the property. Pictures on the website are not accurate. There is a buzzer to get into the door. Police were unseen interviewing. Someone broke down cars in the parking lot homeless people in parking lot not a good area to be in, especially visiting from out of state I would never recommend this hotel to anyone."
Sean 3-night trip
Posted 1 hour ago
The Plaza Inn & Suites

Find out more about Shepherdstown

Search for holiday rentals in Shepherdstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherdstown using one of the methods below:

  • View our selection of featured holiday rentals in Shepherdstown
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Look no further and take a look at our great range of rental properties in 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?

Exclusive Wooded Chalet w Magnificent River Views: Visitors give good reviews to this Shepherdstown vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Shepherdstown?

Expedia has 11 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 Public Library 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.