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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 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 £369
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.
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 place, pet friendly. "
United States
Doug P.
The price is £132
includes taxes & fees
14 Sept - 15 Sept
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

4. 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 £327
includes taxes & fees
9 Sept - 10 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
An outdoor patio with wooden flooring, two white cushioned chairs, and a small table.

5. 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 £247
includes taxes & fees
13 Sept - 14 Sept
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

6. 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, (44 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is £241
includes taxes & fees
13 Sept - 14 Sept
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A two-story house with a porch, green shutters, and a red roof.

7. 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 £256
includes taxes & fees
2 Sept - 3 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry
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, (13 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is £343
includes taxes & fees
3 Sept - 4 Sept
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
A two-story house with a porch and a chimney.

9. Schilling House

Schilling House
3.0 star property
Bolivar
The price is £247
includes taxes & fees
2 Sept - 3 Sept
Schilling House

10. 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 £236
includes taxes & fees
29 Sept - 30 Sept
Cozy Getaway Near History, Hiking & Adventure

11. 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 £169
includes taxes & fees
7 Sept - 8 Sept
Light Horse Inn: Suite 1
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 £235
includes taxes & fees
3 Sept - 4 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.

13. 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 £312
includes taxes & fees
2 Sept - 3 Sept
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
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, (16 reviews)
"Great location for the Spring Festival. The beds were very comfortable. Kitchen was well equipped ."
United States
Renee W.
The price is £333
includes taxes & fees
7 Sept - 8 Sept
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
A two-story house with a front porch, a chimney, and a small garden with pumpkins.

15. Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (154 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is £180
includes taxes & fees
2 Sept - 3 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown
A bedroom with a large bed, a bench, a chair, a nightstand, and a wall with decorative plates.

16. 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, (19 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is £316
includes taxes & fees
2 Sept - 3 Sept
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
A wooden deck with a view of a forested landscape and a sunset.

17. 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 £288
includes taxes & fees
9 Sept - 10 Sept
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
A living room with a stone fireplace, a gray sofa with patterned cushions, and wooden flooring.

18. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (111 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
A wooden staircase with a handrail, a chandelier, and a patterned rug on the floor.

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 £333
includes taxes & fees
13 Sept - 14 Sept
Historic Queen Anne Family Home w Modern Comforts
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

20. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (72 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is £183
includes taxes & fees
2 Sept - 3 Sept
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
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 Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

8/10 Good
"Tight parking."
William 3-night trip
Posted 1 hour ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
888
Accommodation
302 Holiday Homes
Lowest Price
£132
Highest Price
£369