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

Shepherdstown Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Shepherdstown holiday rentals

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

1. ❤️ 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 AU$155
includes taxes & fees
1 Nov - 2 Nov
❤️ Secluded 1940s Romantic Tiny House on the River
A living room with a dining table, chairs, a sofa, and a television.

2. 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 AU$318
includes taxes & fees
22 Oct - 23 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

3. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is AU$439
includes taxes & fees
26 Oct - 27 Oct
Charming Shepherdstown Home - Walk to Downtown
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

4. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
"Very nice place, the lay out is perfect for multiple adults, we stayed for 10 night for work and it was perfect, we will be back for another long stay soon. "
United States
Brandon K.
Walk to Stores: Home in Historic Shepherdstown!
A wooden deck with a grill, outdoor seating, and a bottle of wine.

5. 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.
The price is AU$454
includes taxes & fees
27 Oct - 28 Oct
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.

6. 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 AU$400
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access
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, (76 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 AU$562
includes taxes & fees
4 Nov - 5 Nov
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 AU$532
includes taxes & fees
4 Nov - 5 Nov
Antietam Look Out - Incredible Sunset Views!
A room with large windows, wooden floors, and a ceiling fan.

9. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
The price is AU$461
includes taxes & fees
22 Oct - 23 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

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, (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 AU$338
includes taxes & fees
22 Oct - 23 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A bedroom with a bed, a table, and a view of the outdoors.

11. 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 AU$313
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
A deck with green chairs and a fire pit, surrounded by a house and trees.

12. 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, (33 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is AU$709
includes taxes & fees
3 Nov - 4 Nov
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (60 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is AU$325
includes taxes & fees
2 Nov - 3 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A dining area with a white table and chairs, a fireplace, and a glass coffee table with a magazine.

14. Best location! The Ohio Suite @ historic 1799 Inn

Best location! The Ohio Suite @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (21 reviews)
"Perfect location and the accommodations were inviting, roomy and comfortable. We had a wonderful stay and were very pleased with the suite."
United States
michele b.
The price is AU$346
includes taxes & fees
2 Nov - 3 Nov
Best location! The Ohio Suite @ historic 1799 Inn
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

15. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$439
includes taxes & fees
3 Nov - 4 Nov
Schilling House
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is AU$480
includes taxes & fees
17 Nov - 18 Nov
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

17. 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, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is AU$456
includes taxes & fees
2 Nov - 3 Nov
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A four-poster canopy bed with a view of a cityscape through the window.

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

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (22 reviews)
"Great spot on a cute street. Easy check in and out, and the place is stocked with everything you might need!"
United States
Ashley B.
The price is AU$445
includes taxes & fees
30 Oct - 31 Oct
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
A living room with a TV displaying streaming services, a dining area with a table and chairs, a potted plant, and a wooden cabinet.

19. 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 AU$379
includes taxes & fees
3 Nov - 4 Nov
Top o' the Hill Apt. in historic Harpers Ferry
A cozy attic bedroom with a skylight, a wicker chair, a round table, and a bed with a headboard.

20. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (19 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is AU$464
includes taxes & fees
25 Oct - 26 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
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

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

10/10 Excellent
"Wonderful stay! Would absolutely stay here again!"
Elizabeth 2-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Frederick

Find out more about Shepherdstown

Everything you need to know about Shepherdstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherdstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Shepherdstown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherdstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherdstown holiday rentals we have selected for you start as low as AU$155 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Shepherdstown rentals

At Expedia, we put the best Shepherdstown holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Shepherdstown?

Yes, there are holiday rentals close to the most popular sights in Shepherdstown, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shepherdstown has to offer?

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

How many holiday rentals will I find in Shepherdstown?

Expedia has 10 holiday 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 holiday rental in Shepherdstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shepherdstown. Holiday rentals feature extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.