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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Shepherdstown vacation rentals

A living room with a dining table, chairs, a sofa, and a television.

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is ￥18,959
￥34,818 total
includes taxes & fees
Nov 1 - Nov 2
Quaint Mini Cottage in Shepherdstown - Walking Distance
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (88 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is ￥6,541
￥16,867 total
includes taxes & fees
Nov 8 - Nov 9
❤️ Secluded 1940s Romantic Tiny House on the River
A living room with two leather sofas, a coffee table, and a brick wall.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is ￥27,064
￥54,110 total
includes taxes & fees
Nov 2 - Nov 3
Charming Shepherdstown Home - Walk to Downtown
A kitchen counter with a coffee maker, mugs, and a sign that says "Rise & Shine It's Coffee Time."

4. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
Sharpsburg
10.0 out of 10, Exceptional, (54 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

5. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
The price is ￥23,304
￥44,563 total
includes taxes & fees
Nov 12 - Nov 13
Charming Cabin in the Woods with River Access
A room with large windows, wooden floors, and a ceiling fan.

6. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (101 reviews)
"The cabin was clean, spacious, and"
United States
Daniel
The price is ￥35,498
￥57,195 total
includes taxes & fees
Nov 11 - Nov 12
Antietam Creek - Quiet 2 Bedroom Cabin
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

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, (77 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 ￥20,223
￥68,310 total
includes taxes & fees
Nov 3 - Nov 4
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

8. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"The house was as great! Plenty of space for 5 adults. Conveniently located to the areas we wanted to visit. Very quiet location"
United States
Melisa T.
The price is ￥16,589
￥60,543 total
includes taxes & fees
Nov 4 - Nov 5
Antietam Look Out - Incredible Sunset Views!
A spacious living room with a large window, a wooden coffee table, and a sofa.

9. Schilling House

Schilling House
3.0 star property
Bolivar
The price is ￥38,960
￥49,587 total
includes taxes & fees
Nov 3 - Nov 4
Schilling House
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

10. 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
10.0 out of 10, Exceptional, (52 reviews)
"Very clean Very convenient Very nice stay"
United States
Kevin
The price is ￥22,608
￥47,711 total
includes taxes & fees
Nov 2 - Nov 3
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

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, (56 reviews)
"We had a wonderful stay: The place was adorable, spotless, and had everything we needed for a relaxing getaway. It was cozy, well-maintained, and in a great location for exploring Harper’s Ferry. We’re staying here again in a couple months!"
United States
Hannah P.
The price is ￥22,909
￥39,785 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

12. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is ￥43,447
￥71,844 total
includes taxes & fees
Nov 4 - Nov 5
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A deck with green chairs and a fire pit, surrounded by a house and trees.

13. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (34 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is ￥36,641
￥94,440 total
includes taxes & fees
Nov 22 - Nov 23
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (35 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 ￥30,761
￥53,641 total
includes taxes & fees
Nov 1 - Nov 2
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A bedroom with a bed, a table, and a view of the outdoors.

15. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is ￥21,999
￥35,057 total
includes taxes & fees
Nov 9 - Nov 10
The Carriage House at Carrot Top Cottage
A two-story house with a porch, green shutters, and a red roof.

16. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (59 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
The price is ￥34,132
￥66,097 total
includes taxes & fees
Nov 4 - Nov 5
Enchanting Cottage, walk to Downtown Harpers Ferry
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

17. 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, (16 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is ￥33,371
￥74,477 total
includes taxes & fees
Nov 12 - Nov 13
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A hammock on a grassy area with a view of a river and forested hills.

18. La Soledad Lavender Farm on the Potomac

La Soledad Lavender Farm on the Potomac
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Terrific place and very friendly and accommodating host"
United States
Michel R.
The price is ￥47,397
￥68,277 total
includes taxes & fees
Nov 11 - Nov 12
La Soledad Lavender Farm on the Potomac
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (61 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is ￥21,439
￥36,202 total
includes taxes & fees
Nov 4 - Nov 5
Best location! The Pullman Apt @ historic 1799 Inn
A living room with a TV displaying streaming services, a dining area with a table and chairs, a potted plant, and a wooden cabinet.

20. Top o' the Hill Apt. in historic Harpers Ferry

Top o' the Hill Apt. in historic Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (64 reviews)
"Clean and welcoming with adequate parking for all guests."
United States
Linda
The price is ￥25,914
￥41,888 total
includes taxes & fees
Nov 4 - Nov 5
Top o' the Hill Apt. in historic Harpers Ferry
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

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

10/10 Excellent
"Very helpful staff"
Blake 1-night trip
Posted less than an hour ago
Clarion Inn Harpers Ferry - Charles Town

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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  • Enter your travel dates to view the best deals on holiday rentals in Shepherdstown while they last

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?

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.