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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Shepherdstown holiday homes

Dining

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 AU$773
includes taxes & fees
9 Sept - 10 Sept
Exclusive Wooded Chalet w Magnificent River Views
Terrace/patio

2. Cozy Getaway Near History, Hiking & Adventure

Cozy Getaway Near History, Hiking & Adventure
Bolivar
10.0 out of 10, Exceptional, (1 review)
The price is AU$421
includes taxes & fees
8 Sept - 9 Sept
Cozy Getaway Near History, Hiking & Adventure
Smart TV

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
The price is AU$304
includes taxes & fees
24 Aug - 25 Aug
Cozy Downtown Cabin - Family Friendly
TV, fireplace

4. Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia

Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia
The Woods
The price is AU$348
includes taxes & fees
26 Aug - 27 Aug
Cute Secluded Cabin with Fire Pit in Hedgesville, West Virginia
Exterior

5. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AU$471
includes taxes & fees
20 Sept - 21 Sept
Schilling House
Exterior

6. 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 AU$248
includes taxes & fees
22 Aug - 23 Aug
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

7. 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.
The price is AU$352
includes taxes & fees
1 Sept - 2 Sept
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Interior

8. 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, (65 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is AU$638
includes taxes & fees
8 Sept - 9 Sept
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Terrace/patio

9. Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (42 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is AU$433
includes taxes & fees
24 Aug - 25 Aug
Icy…New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Exterior

10. 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$364
includes taxes & fees
24 Aug - 25 Aug
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Smart TV, fireplace, DVD player, books

11. 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.
The price is AU$552
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Terrace/patio

12. 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, (25 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 AU$736
includes taxes & fees
26 Aug - 27 Aug
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Interior

13. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.4 out of 10, Exceptional, (6 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$510
includes taxes & fees
23 Aug - 24 Aug
New, Contemporary House in Historic Harpers Ferry
Terrace/patio

14. 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)
"Beautiful home; beds are very comfortable. Atmosphere very comforting. Kitchen well stocked. Would come again and will tell others great place to stay."
United States
Penny M.
The price is AU$507
includes taxes & fees
27 Aug - 28 Aug
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Exterior

15. 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 AU$463
includes taxes & fees
8 Sept - 9 Sept
Enchanting Cottage, walk to Downtown Harpers Ferry
Interior

16. 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.
Light Horse Inn: Suite 1
2 bedrooms, travel cot, WiFi, bed sheets

17. Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"Great spot"
China
Clara
The price is AU$431
includes taxes & fees
31 Aug - 1 Sept
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Microwave, oven, stovetop, dishwasher

18. 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)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is AU$618
includes taxes & fees
27 Aug - 28 Aug
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Coffee/tea maker, fridge, microwave, oven

19. 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, (71 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AU$353
includes taxes & fees
25 Aug - 26 Aug
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Outdoor dining

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, (34 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AU$568
includes taxes & fees
24 Aug - 25 Aug
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 Harpers Ferry - Charles Town

Quality Inn Harpers Ferry - Charles Town

8/10 Good
"We enjoyed our stay, but found there was no elevator so getting bags up the stairs was somewhat tricky. The room was clean, the space was nice, and parking was easy. Overall a good experience."
Janna 1-night trip
Posted 2 hours ago
Quality Inn Harpers Ferry - Charles Town

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
742
Accommodation
293 Holiday Homes
Lowest Price
AU$248
Highest Price
AU$773