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

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Shepherdstown holiday homes

A spacious living area with a dining table, blue chairs, and a wooden floor.

1. 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$2,227
HK$3,848 total
includes taxes & fees
7 Sept - 8 Sept
Exclusive Wooded Chalet w Magnificent River Views
A nighttime forest path lit by string lights.

2. 5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (50 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 HK$588
HK$1,997 total
includes taxes & fees
1 Sept - 2 Sept
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
A two-story house with a porch, stone foundation, and a flag.

3. 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, (210 reviews)
"Great value, such a cool house, we hope to come again!"
United States
philip g.
The price is HK$1,137
HK$1,379 total
includes taxes & fees
31 Aug - 1 Sept
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

4. Antietam House Historic Sharpsburg Retreat

Antietam House Historic Sharpsburg Retreat
Sharpsburg
8.8 out of 10, Excellent, (3 reviews)
"The house is a perfect spot for walking to the battlefield"
United States
Karen
Antietam House Historic Sharpsburg Retreat
A deck with green chairs and a fire pit, surrounded by a house and trees.

5. 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, (25 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
The price is HK$1,647
HK$4,537 total
includes taxes & fees
3 Sept - 4 Sept
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

6. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is HK$1,432
HK$3,396 total
includes taxes & fees
9 Sept - 10 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A house with a well-lit entrance, a small garden, and a gravel driveway.

7. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

8. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location and property."
United States
Helen F.
The price is HK$705
HK$2,093 total
includes taxes & fees
30 Aug - 31 Aug
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

9. 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, (58 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is HK$1,090
HK$2,306 total
includes taxes & fees
31 Aug - 1 Sept
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A two-story house with a porch, green shutters, and a red roof.

10. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (54 reviews)
"Area was great, host was super helpful and communicative "
United States
Riya L.
The price is HK$1,428
HK$2,745 total
includes taxes & fees
31 Aug - 1 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry
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, (43 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is HK$1,185
HK$2,430 total
includes taxes & fees
31 Aug - 1 Sept
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A room with a large sliding glass door leading to a backyard with a grassy lawn and trees. There are two gray upholstered chairs in the room.

12. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.4 out of 10, Exceptional, (6 reviews)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
The price is HK$784
HK$2,907 total
includes taxes & fees
30 Aug - 31 Aug
New, Contemporary House in Historic Harpers Ferry

13. Schilling House

Schilling House
3.0 star property
Bolivar
The price is HK$2,148
HK$2,690 total
includes taxes & fees
30 Aug - 31 Aug
Schilling House

14. Light Horse Inn: Suite 1

Light Horse Inn: Suite 1
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful in every way! From the staff , the inn it’s self, location and even more. Will definitely be back."
United States
Angie K.
The price is HK$1,372
HK$1,762 total
includes taxes & fees
3 Sept - 4 Sept
Light Horse Inn: Suite 1

15. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (1 review)
"This is a great property. Very clean and well taken care of. Backyard is fantastic too! You won’t be sorry you stayed here. Close to historic town and lots of great places to eat. Beautiful area!"
United States
Kelly
The price is HK$1,323
HK$2,490 total
includes taxes & fees
2 Sept - 3 Sept
Cozy Getaway Near History, Hiking & Adventure
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

16. 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, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
The price is HK$2,156
HK$3,564 total
includes taxes & fees
7 Sept - 8 Sept
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A four-poster canopy bed with a view of a cityscape through the window.

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

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (21 reviews)
"Great spot"
China
Clara
The price is HK$1,411
HK$2,444 total
includes taxes & fees
31 Aug - 1 Sept
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
An outdoor dining area with a table set for two, surrounded by chairs, and a grill on the right.

18. New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (35 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is HK$1,223
HK$3,264 total
includes taxes & fees
30 Aug - 31 Aug
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

19. 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, (13 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is HK$1,490
HK$3,493 total
includes taxes & fees
30 Aug - 31 Aug
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A wooden deck with a view of a forested landscape and a sunset.

20. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
8.8 out of 10, Excellent, (12 reviews)
"House was clean and loaded with required amenities. We loved the backyard view and the proximity to the lakeside picnic area."
United States
henu m.
The price is HK$1,411
HK$3,043 total
includes taxes & fees
31 Aug - 1 Sept
A peaceful, forest retreat with stunning views near 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

Days Inn by Wyndham Frederick

Days Inn by Wyndham Frederick

8/10 Good
"Great, Quiet and Peaceful area."
Teresa 4-night trip
Posted 5 hours ago
Days Inn by Wyndham Frederick

Find out more about Shepherdstown

Shepherdstown Vacation Homes information

Number of reviews
631
Accommodation
302 Vacation Homes
Lowest Price
HK$1,379
Highest Price
HK$4,537

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