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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Shepherdstown vacation homes

A kitchen with wooden cabinets, a stainless steel refrigerator, and a microwave.

1. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is ￥26,012
￥50,069 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥79,711
￥140,999 total
includes taxes & fees
Oct 14 - Oct 15
Exclusive Wooded Chalet w Magnificent River Views
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

3. 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.
Antietam House Historic Sharpsburg Retreat
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)
The price is ￥21,174
￥45,585 total
includes taxes & fees
Oct 12 - Oct 13
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
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, (31 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is ￥24,484
￥80,552 total
includes taxes & fees
Oct 19 - Oct 20
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
KITCHEN/LIVING ROOM - 2nd floor long view showing the whole space, tv, wifi

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.
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)
The price is ￥13,509
￥40,887 total
includes taxes & fees
Oct 13 - Oct 14
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A kitchen with a countertop, a kettle, a coffee maker, a microwave, and wall-mounted shelves with decorative items.

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 ￥20,382
￥64,682 total
includes taxes & fees
Oct 25 - Oct 26
New, Contemporary House in Historic Harpers Ferry
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

9. 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 ￥23,628
￥52,397 total
includes taxes & fees
Nov 9 - Nov 10
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is ￥23,542
￥48,081 total
includes taxes & fees
Oct 13 - Oct 14
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

11. 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 ￥22,896
￥51,384 total
includes taxes & fees
Oct 30 - Oct 31
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A four-poster canopy bed with a view of a cityscape through the window.

12. 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)
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

13. Schilling House

Schilling House
3.0 star property
Bolivar
The price is ￥43,265
￥54,189 total
includes taxes & fees
Oct 11 - Oct 12
Schilling House
A modern kitchen with wooden cabinets, a large island with stools, and a bar area.

14. 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 ￥43,423
￥71,804 total
includes taxes & fees
Oct 19 - Oct 20
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A living room with two dark sofas, a wooden coffee table, and a chandelier.

15. 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 ￥35,316
￥81,172 total
includes taxes & fees
Nov 3 - Nov 4
Cozy Getaway Near History, Hiking & Adventure
A modern kitchen with a central island, stainless steel appliances, and a stone accent wall.

16. 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)
The price is ￥33,352
￥74,265 total
includes taxes & fees
Oct 14 - Oct 15
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.

17. 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 ￥55,998
￥89,140 total
includes taxes & fees
Nov 4 - Nov 5
Enchanting Cottage, walk to Downtown Harpers Ferry
A staircase with white steps and a wooden handrail, leading to a dining area with a table and chairs.

18. 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 ￥48,081
￥93,743 total
includes taxes & fees
Nov 9 - Nov 10
The Retreat at Harpers Ferry
A residential area with houses, a large building, and a river.

19. 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 ￥41,699
￥76,803 total
includes taxes & fees
Oct 20 - Oct 21
Historic Queen Anne Family Home w Modern Comforts
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
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 ￥31,580
￥64,505 total
includes taxes & fees
Nov 2 - Nov 3
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

Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

8/10 Good
"Rooms were great! Staff was friendly. Parking was good. The only downside was the breakfast options. Selections were slim."
Micah 1-night trip
Posted 11 hours ago
Fairfield Inn & Suites by Marriott Hagerstown

Find out more about Shepherdstown

Shepherdstown Vacation Homes information

Number of reviews
358
Accommodation
302 Vacation Homes
Lowest Price
￥40,887
Highest Price
￥140,999