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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Shepherdstown holiday homes

A window with a view of a grassy yard and trees.

1. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is AU$406
includes taxes & fees
13 Oct - 14 Oct
Charming Shepherdstown Home - Walk to Downtown
A house with a deck, outdoor seating, and a fire pit.

2. 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 AU$1,080
includes taxes & fees
6 Oct - 7 Oct
Exclusive Wooded Chalet w Magnificent River Views
A house with a well-lit entrance, a small garden, and a gravel driveway.

3. 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.
The price is AU$373
includes taxes & fees
6 Oct - 7 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

4. 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, (48 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is AU$419
includes taxes & fees
8 Oct - 9 Oct
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

5. 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 AU$651
includes taxes & fees
6 Oct - 7 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
A room with a white desk, shelves with patterned fabric, a blue chair, and a patterned carpet.

6. 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 AU$477
includes taxes & fees
6 Oct - 7 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

7. 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 AU$470
includes taxes & fees
30 Oct - 31 Oct
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A single-story building with a gabled roof, a front porch, and a small deck area.

8. 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 AU$540
includes taxes & fees
8 Oct - 9 Oct
New, Contemporary House in Historic 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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is AU$445
includes taxes & fees
13 Oct - 14 Oct
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A four-poster canopy bed with a view of a cityscape through the window.

10. 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 AU$443
includes taxes & fees
18 Oct - 19 Oct
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

11. 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, (18 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is AU$645
includes taxes & fees
19 Oct - 20 Oct
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

12. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$451
includes taxes & fees
13 Oct - 14 Oct
Schilling House
A living room with two dark sofas, a wooden coffee table, and a chandelier.

13. 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 AU$498
includes taxes & fees
7 Oct - 8 Oct
Cozy Getaway Near History, Hiking & Adventure
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

14. 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 AU$789
includes taxes & fees
7 Oct - 8 Oct
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A two-story house with a porch, green shutters, and a red roof.

15. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (57 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 AU$792
includes taxes & fees
13 Oct - 14 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

16. Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts
Harpers Ferry
9.2 out of 10, Wonderful, (9 reviews)
"This was a wonderful vacation rental--clean, beautifully appointed, and located within walking distance of historic Harpers Ferry and the AT. We couldn't have asked for a nicer place to spend our long weekend getaway."
United States
Jenny H.
The price is AU$531
includes taxes & fees
3 Nov - 4 Nov
Historic Queen Anne Family Home w Modern Comforts
A staircase with white steps and a wooden handrail, leading to a dining area with a table and chairs.

17. The Retreat at Harpers Ferry

The Retreat at Harpers Ferry
Bolivar
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful stay. House was lovely. Back yard / gazebo fabulous for hanging out. Everything you needed in home from the stocked coffee bar down to Q-tips. Within walking distance to some interesting entertainment & cafes. Very pleasant stay. Will do again."
United States
Tonia Y.
The price is AU$812
includes taxes & fees
6 Oct - 7 Oct
The Retreat at Harpers Ferry
A wooden deck with a view of a forested landscape and a sunset.

18. 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 AU$548
includes taxes & fees
6 Oct - 7 Oct
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

19. 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, (21 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is AU$595
includes taxes & fees
6 Oct - 7 Oct
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A dining area with a glass table surrounded by chairs, a living room in the background, and a window with white curtains.

20. Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!

Charming 3-Bedroom Home in historic Harpers Ferry: Pet Friendly!
Harpers Ferry
10.0 out of 10, Exceptional, (44 reviews)
"We loved this property! It was a perfect distance to the shops and restaurants in Harper’s Ferry. The house is beautiful and comfortable and even had some perks for our dog."
United States
Melissa V.
The price is AU$689
includes taxes & fees
7 Oct - 8 Oct
Charming 3-Bedroom Home in historic Harpers Ferry: 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

Comfort Inn Frederick - Ballenger Creek

Comfort Inn Frederick - Ballenger Creek

8/10 Good
"1. It was a great value compared to other hotels in the area 2. The rooms could use updating 3. The breakfast was not great. The eggs and sausage were not good, but there are other options, so all in all, breakfast was okay at best."
Gerry 4-night trip
Posted 3 hours ago
Comfort Inn Frederick - Ballenger Creek

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
388
Accommodation
301 Holiday Homes
Lowest Price
AU$373
Highest Price
AU$1,080