Holiday Homes in Shepherdstown

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Shepherdstown holiday homes

Dining

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (17 reviews)
"The entire stay was wonderful. Fantastic views. "
United States
Downer F.
The price is NZ$791
includes taxes & fees
27 Apr - 28 Apr
Exclusive Wooded Chalet w Magnificent River Views

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.4 out of 10, Exceptional, (125 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is NZ$486
includes taxes & fees
20 Apr - 21 Apr
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Exterior

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (143 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is NZ$423
includes taxes & fees
17 Apr - 18 Apr
Charming "Cream of the Crop" Cape ~❤️of Middletown
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.0 out of 10, Wonderful, (83 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is NZ$476
includes taxes & fees
22 Apr - 23 Apr
Luxury Condo In Downtown Frederick
Outdoor dining

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Frederick
10.0 out of 10, Exceptional, (40 reviews)
"Laura is a fantastic host and the apartment is beautiful. It’s convenient to all sites and amenities in downtown Frederick, but tucked away so you can enjoy a feeling of home. There are great coffee shops nearby and it’s easy to hop on the highway to see local wineries. "
United States
Thomas L.
The price is NZ$425
includes taxes & fees
21 Apr - 22 Apr
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (61 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is NZ$421
includes taxes & fees
20 Apr - 21 Apr
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Exterior

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, (199 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is NZ$296
includes taxes & fees
17 Apr - 18 Apr
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.6 out of 10, Good, (27 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is NZ$505
includes taxes & fees
21 Apr - 22 Apr
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Outdoor dining

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"The house was very nice and the hosts were communicative and provided everything we needed."
United States
Jackie C.
The price is NZ$746
includes taxes & fees
19 Apr - 20 Apr
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Interior

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, (60 reviews)
"Great location, spacious living area, plenty of linens, and excellent fire pit! "
United States
Maria Elena S.
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Casino

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, (44 reviews)
"We only stayed 2 nights for a little getaway, but this fit the bill perfectly. Everything was clean and comfortable, and the host was very responsive. Will be looking to stay again when the weather is warmer! "
United States
Matthew M.
The price is NZ$519
includes taxes & fees
22 Apr - 23 Apr
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Interior

Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is NZ$683
includes taxes & fees
21 Apr - 22 Apr
Stone Cabin on Valley View: Fire Pit + Hot Tub
Fridge, microwave, oven, dishwasher

Riverview Retreat - Pool, Hot Tub, and Mtn Views!

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"We had a great time at Riverview Retreat! The house was perfect for our group and offered beautiful views. We especially loved the fireplace and all of the amenities they had available. The hot tub code was missing from the manual so we weren't able to use it on our first night and the spiral staircase was pretty intimidating for the weather we had. Heed the warnings about needing four wheel drive in the winter for the driveway. I was thankful there wasn't snow as it would have been scary to...
United States
Stacy H.
The price is NZ$695
includes taxes & fees
20 Apr - 21 Apr
Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Property grounds

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (67 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
The price is NZ$677
includes taxes & fees
30 Apr - 1 May
Terra Alta - Incredible River Views and Hot Tub!
Terrace/patio

Harpers Ferry Mountain Escape w/ Patio & Fireplace

Harpers Ferry Mountain Escape w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Great location and amenities, super clean and the smores were a nice bonus "
United States
William S.
Harpers Ferry Mountain Escape w/ Patio & Fireplace
Exterior

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
10.0 out of 10, Exceptional, (22 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is NZ$436
includes taxes & fees
19 Apr - 20 Apr
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Interior

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, (7 reviews)
"Great setup. Very clean and well organized. Had everything we needed. Loved the barrel sauna and back porch. "
United States
Gary B.
The price is NZ$782
includes taxes & fees
19 Apr - 20 Apr
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is NZ$623
includes taxes & fees
6 May - 7 May
Bluemont home just minutes to wineries, breweries, hiking and more!
Microwave, oven, stovetop, dishwasher

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, (7 reviews)
"Beautiful historic home. Hosts were very welcoming and the place was newly renovated. "
United States
Drew M.
The price is NZ$704
includes taxes & fees
23 Apr - 24 Apr
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (47 reviews)
"Prime location for all things in Harpers Ferry!! "
United States
Annette K.
The price is NZ$523
includes taxes & fees
22 Apr - 23 Apr
Enchanting Cottage, walk to Downtown 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

Tru By Hilton Martinsburg

Tru By Hilton Martinsburg

8/10 Good
"Property is brand new, clean and comfortable. Room is a bit small, with no microwave. However, it is comfortable and in a convenient location. Front desk staff was very professional and caring."
Michael 3-night trip
Posted 3 hours ago
Tru By Hilton Martinsburg

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
817
Accommodation
308 Holiday Homes
Lowest Price
NZ$296
Highest Price
NZ$791