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
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 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 NZ$537
includes taxes & fees
27 Oct - 28 Oct
Charming Shepherdstown Home - Walk to Downtown
A hallway with wooden flooring, a staircase, a door with a white frame, a lamp on a small table, and a wall-mounted mirror.

2. 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 NZ$577
includes taxes & fees
22 Oct - 23 Oct
Antietam House Historic Sharpsburg Retreat
A deck with green chairs and a fire pit, surrounded by a house and trees.

3. 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 NZ$878
includes taxes & fees
18 Oct - 19 Oct
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
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, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is NZ$508
includes taxes & fees
18 Oct - 19 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 NZ$813
includes taxes & fees
28 Oct - 29 Oct
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.

6. 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 NZ$462
includes taxes & fees
21 Oct - 22 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A spacious kitchen with modern appliances, a dining area with a large table, and a living room with a sofa and a fireplace.

7. Camp Patowmack - Riverfront, Hot Tub, and Sauna!

Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)
"Great water access"
United States
claire r.
The price is NZ$1,193
includes taxes & fees
3 Nov - 4 Nov
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
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 NZ$534
includes taxes & fees
13 Nov - 14 Nov
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, (62 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is NZ$549
includes taxes & fees
21 Oct - 22 Oct
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

10. 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 NZ$585
includes taxes & fees
18 Oct - 19 Oct
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

11. 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 NZ$699
includes taxes & fees
29 Oct - 30 Oct
Historic Queen Anne Family Home w Modern Comforts
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)
"Great spot"
China
Clara
The price is NZ$543
includes taxes & fees
29 Oct - 30 Oct
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 NZ$548
includes taxes & fees
25 Oct - 26 Oct
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, (19 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is NZ$800
includes taxes & fees
2 Nov - 3 Nov
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 NZ$866
includes taxes & fees
29 Oct - 30 Oct
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)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is NZ$824
includes taxes & fees
9 Nov - 10 Nov
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, (58 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 NZ$671
includes taxes & fees
21 Oct - 22 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
A hammock on a grassy area with a view of a river and forested hills.

18. La Soledad Lavender Farm on the Potomac

La Soledad Lavender Farm on the Potomac
Harpers Ferry
10.0 out of 10, Exceptional, (32 reviews)
"Terrific place and very friendly and accommodating host"
United States
Michel R.
The price is NZ$754
includes taxes & fees
11 Nov - 12 Nov
La Soledad Lavender Farm on the Potomac
A staircase with white steps and a wooden handrail, leading to a dining area with a table and chairs.

19. 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 NZ$996
includes taxes & fees
19 Oct - 20 Oct
The Retreat at Harpers Ferry
An outdoor dining area with a table set for two, surrounded by chairs, and a grill on the right.

20. 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, (38 reviews)
"A very quiet and relaxing spot to spend with family."
United States
Stephanie T.
The price is NZ$726
includes taxes & fees
18 Oct - 19 Oct
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
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

Quality Inn Shepherdstown

Quality Inn Shepherdstown

10/10 Excellent
"Great"
Terry 1-night trip
Posted 14 hours ago
Quality Inn Shepherdstown

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
450
Accommodation
297 Holiday Homes
Lowest Price
NZ$462
Highest Price
NZ$1,193