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

Holiday Homes in Shepherdstown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Shepherdstown holiday homes

A spacious living room with a staircase, a sofa, a television, and a large window.

1. BEST LOCATION: Historic Shepherdstown Getaway

BEST LOCATION: Historic Shepherdstown Getaway
Shepherdstown
10.0 out of 10, Exceptional, (112 reviews)
"Wonderful host, great location, everything was a expected"
United States
Dave D.
The price is €365
includes taxes & fees
28 Sept - 29 Sept
BEST LOCATION: Historic Shepherdstown Getaway

2. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is €242
includes taxes & fees
28 Sept - 29 Sept
Charming Shepherdstown Home - Walk to Downtown
A house with a deck, outdoor seating, and a fire pit.

3. 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 €644
includes taxes & fees
14 Oct - 15 Oct
Exclusive Wooded Chalet w Magnificent River Views
A large, curved metal building with a covered entrance and two chairs outside.

4. Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!

Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
Sharpsburg
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed the views."
United States
Shena M.
Antietam Dome: Level 2 Charger, 1 level, Walk to C&O Canal at Antietam Aqueduct Relax, Naturally!
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

5. 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 €316
includes taxes & fees
19 Oct - 20 Oct
Antietam House Historic Sharpsburg Retreat

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 €398
includes taxes & fees
6 Oct - 7 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A hallway with wooden flooring, a ceiling fan, and a door leading to a room with a bed.

7. Schilling House

Schilling House
3.0 star property
Bolivar
The price is €300
includes taxes & fees
27 Sept - 28 Sept
Schilling House
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

8. 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, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is €406
includes taxes & fees
27 Sept - 28 Sept
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A deck with green chairs and a fire pit, surrounded by a house and trees.

9. 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, (30 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 €495
includes taxes & fees
1 Oct - 2 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

10. 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, (61 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is €259
includes taxes & fees
21 Oct - 22 Oct
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
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.

11. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (8 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 €326
includes taxes & fees
28 Sept - 29 Sept
New, Contemporary House in Historic Harpers Ferry
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

12. 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, (47 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is €282
includes taxes & fees
29 Sept - 30 Sept
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

13. 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.
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A living room with two dark sofas, a wooden coffee table, and a chandelier.

14. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (2 reviews)
"This house was perfect for our getaway. Clean and comfortable. Close to everything."
United States
Ashlee O.
The price is €274
includes taxes & fees
28 Sept - 29 Sept
Cozy Getaway Near History, Hiking & Adventure
A wooden deck with a view of a forested landscape and a sunset.

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

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.0 out of 10, Wonderful, (14 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 €345
includes taxes & fees
28 Sept - 29 Sept
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
A four-poster canopy bed with a view of a cityscape through the window.

16. 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 €269
includes taxes & fees
1 Oct - 2 Oct
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.

17. 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, (36 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is €453
includes taxes & fees
25 Sept - 26 Sept
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

18. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (20 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

19. 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, (17 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A modern living room with a sofa, chairs, a coffee table, and a TV on a stand.

20. A private home in historic Bolivar with a hot tub and yard. Pet friendly!

A private home in historic Bolivar with a hot tub and yard. Pet friendly!
Bolivar
10.0 out of 10, Exceptional, (35 reviews)
"Lovely place to stay! "
United States
April O.
The price is €370
includes taxes & fees
29 Sept - 30 Sept
A private home in historic Bolivar with a hot tub and yard. Pet friendly!
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

10/10 Excellent
"The whole property was clean from inside out. It smell good overall it was a very good stay."
Nicole 2-night trip
Posted 20 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
482
Accommodation
302 Holiday Homes
Lowest Price
€242
Highest Price
€644