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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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, (87 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 HK$325
HK$838 total
includes taxes & fees
25 Oct - 26 Oct
❤️ 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 HK$942
HK$1,738 total
includes taxes & fees
18 Oct - 19 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
Charming Shepherdstown Home - Walk to Downtown
A house with a deck, outdoor seating, and a fire pit.

4. 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 HK$3,877
HK$6,895 total
includes taxes & fees
11 Nov - 12 Nov
Exclusive Wooded Chalet w Magnificent River Views
Terrace/patio

5. 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 HK$7,551
HK$9,597 total
includes taxes & fees
10 Nov - 11 Nov
Gorgeous Cabin with Magnificent Views of the Potomac River in Shepherdstown, West Virginia
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

6. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
The price is HK$879
HK$2,913 total
includes taxes & fees
2 Nov - 3 Nov
Antietam Look Out - Incredible Sunset Views!
A room with large windows, wooden floors, and a ceiling fan.

7. 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 HK$1,570
HK$2,579 total
includes taxes & fees
15 Oct - 16 Oct
Antietam Creek - Quiet 2 Bedroom Cabin
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

8. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
9.0 out of 10, Wonderful, (4 reviews)
"My friends and I had a wonderful time here for Labor Day! Quiet and a great location for all sorts of activities."
United States
Nick W.
The price is HK$1,123
HK$2,563 total
includes taxes & fees
22 Oct - 23 Oct
Antietam House Historic Sharpsburg Retreat
A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

9. 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 HK$1,311
HK$3,633 total
includes taxes & fees
20 Oct - 21 Oct
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

10. Schilling House

Schilling House
3.0 star property
Bolivar
The price is HK$2,150
HK$2,693 total
includes taxes & fees
18 Oct - 19 Oct
Schilling House
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

11. 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 HK$1,052
HK$2,282 total
includes taxes & fees
18 Oct - 19 Oct
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.

12. 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, (53 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 HK$1,138
HK$1,993 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Rustic Walkout Basement Cabin in Historic 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 HK$1,065
HK$1,798 total
includes taxes & fees
1 Nov - 2 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

14. 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, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
The price is HK$1,174
HK$2,604 total
includes taxes & fees
15 Oct - 16 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
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, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is HK$1,093
HK$1,733 total
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.

16. 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, (32 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is HK$1,151
HK$3,915 total
includes taxes & fees
18 Oct - 19 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

17. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (70 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
The price is HK$777
HK$1,414 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

18. Best location! Baltimore Suite @ historic 1799 Inn

Best location! Baltimore Suite @ historic 1799 Inn
Harpers Ferry
9.6 out of 10, Exceptional, (12 reviews)
The price is HK$1,204
HK$1,970 total
includes taxes & fees
1 Nov - 2 Nov
Best location! Baltimore Suite @ 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.

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 HK$1,287
HK$2,081 total
includes taxes & fees
1 Nov - 2 Nov
Top o' the Hill Apt. in historic Harpers Ferry
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is HK$1,169
HK$2,405 total
includes taxes & fees
21 Oct - 22 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

Best Western Historic Frederick

Best Western Historic Frederick

10/10 Excellent
"Overall a nice place with a great staff. I had a late checkout and the room was a little noisy in the morning (I could hear the cleaning staff and the room next to mine getting ready to leave) but it wasn’t too bad."
David 1-night trip
Posted 2 hours ago
Best Western Historic Frederick

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
  • Use the map to find apartments and other holiday homes in the Shepherdstown neighbourhood you prefer
  • 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 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.