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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Shepherdstown holiday homes

Exterior

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia

"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia
Shepherdstown
The price is £104
includes taxes & fees
1 Jun - 2 Jun
"Lovely Tiny House Rental for a Romantic Getaway in Shepherdstown, West Virginia

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, (126 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is £195
includes taxes & fees
1 Jun - 2 Jun
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, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is £222
includes taxes & fees
1 Jun - 2 Jun
Charming "Cream of the Crop" Cape ~❤️of Middletown
Outdoor dining

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (17 reviews)
"The house was spotless, and exactly where we needed/wanted to be. It was close to everything we wanted to see and we definitely will use it again!"
United States
Janet L.
The price is £213
includes taxes & fees
3 Jun - 4 Jun
Chic, pets, walk to downtown
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, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is £133
includes taxes & fees
3 Jun - 4 Jun
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Dining

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (90 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is £238
includes taxes & fees
10 Jun - 11 Jun
Luxury Condo In Downtown Frederick
Property grounds

The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is £272
includes taxes & fees
31 May - 1 Jun
The Blue Jay | New House in the Woods w/ Hot Tub
Terrace/patio

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (11 reviews)
"We had a great stay "
United States
Lauren O.
The price is £298
includes taxes & fees
4 Jun - 5 Jun
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
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, (44 reviews)
"Immaculate apartment conveniently located close to Frederick Health Hospital in a quiet residential neighborhood. Just a fifteen minute walk to the heart of Frederick for memorable dining, interesting shops, and cozy cafés."
United States
Mark L.
The price is £205
includes taxes & fees
9 Jun - 10 Jun
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, (63 reviews)
"The Host Heather have the most beautiful personality. She was very helpful. Told us the history of the home which we was able to appreciate everything about this beautiful home."
United States
Samira A.
The price is £239
includes taxes & fees
9 Jun - 10 Jun
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Fridge, microwave, oven, stovetop

Fell like home one hour away from Washington DC private parking and patio

Fell like home one hour away from Washington DC private parking and patio
Hagerstown
7.0 out of 10, Good, (2 reviews)
"great"
United States
mike c.
The price is £109
includes taxes & fees
30 May - 31 May
Fell like home one hour away from Washington DC private parking and patio
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 £345
includes taxes & fees
1 Jun - 2 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Outdoor dining

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.6 out of 10, Exceptional, (5 reviews)
The price is £192
includes taxes & fees
3 Jun - 4 Jun
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
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
7.4 out of 10, Good, (28 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 £238
includes taxes & fees
3 Jun - 4 Jun
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
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
8.4 out of 10, Very good, (62 reviews)
"Great location, spacious living area, plenty of linens, and excellent fire pit! "
United States
Maria Elena S.
The price is £319
includes taxes & fees
3 Jun - 4 Jun
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Smart TV, fireplace

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is £293
includes taxes & fees
1 Jun - 2 Jun
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

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, (23 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is £194
includes taxes & fees
10 Jun - 11 Jun
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Property grounds

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is £297
includes taxes & fees
3 Jun - 4 Jun
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Interior

A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is £286
includes taxes & fees
1 Jun - 2 Jun
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Exterior

Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (51 reviews)
"Prime location for all things in Harpers Ferry!! "
United States
Annette K.
The price is £230
includes taxes & fees
1 Jun - 2 Jun
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

10/10 Excellent
"Very nice and accommodating staff, breakfast was ready early, clean everything."
Nathan 1-night trip
Posted 1 hour ago
Tru By Hilton Martinsburg

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
861
Accommodation
308 Holiday Homes
Lowest Price
£109
Highest Price
£345