Holiday Homes in Shepherdstown

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Our top choices for Shepherdstown holiday homes

Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (19 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is €588
includes taxes & fees
28 Jun - 29 Jun
Exclusive Wooded Chalet w Magnificent River Views

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)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is €244
includes taxes & fees
19 Jul - 20 Jul
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

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

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is €405
includes taxes & fees
23 Jun - 24 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!

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 €254
includes taxes & fees
14 Jul - 15 Jul
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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, (129 reviews)
"Great stay, excellent location and host was always readily available. Highly recommended!"
United States
Zayde C.
The price is €243
includes taxes & fees
6 Jul - 7 Jul
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (18 reviews)
"We really enjoyed our recent stay. Check-in was simple, the host very responsive, location is excellent (we walked everywhere) and well designed. Would stay again."
United States
Richard M.
Chic, pets, walk to downtown

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (94 reviews)
"All amenities were top notch "
United States
John M.
The price is €305
includes taxes & fees
8 Jul - 9 Jul
Luxury Condo In Downtown Frederick

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is €286
includes taxes & fees
29 Jun - 30 Jun
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

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 €358
includes taxes & fees
24 Jun - 25 Jun
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (147 reviews)
"An absolutely charming getaway spot tucked in a small town with trendy shops and eateries. Our host gave fabulous recommendations and the property was spotless, cozy and well equipped for the perfect weekend getaway."
United States
Jennifer P.
The price is €306
includes taxes & fees
11 Jul - 12 Jul
Charming "Cream of the Crop" Cape ~❤️of Middletown

Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
9.0 out of 10, Wonderful, (26 reviews)
"House was very clean and well stocked! Very comfortable and within short distance of a lovely town Berkley Springs."
United States
Annie W.
The price is €237
includes taxes & fees
23 Jun - 24 Jun
Modern, family-friendly, nature packed getaway

Inns of Whitetail #108

Inns of Whitetail #108
Mercersburg
6.0 out of 10, (2 reviews)
"Absolutely amazing ! Very clean and Check in was super easy . "
United States
Tiffany B.
The price is €241
includes taxes & fees
23 Jun - 24 Jun
Inns of Whitetail #108

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (71 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 €491
includes taxes & fees
5 Jul - 6 Jul
Terra Alta - Incredible River Views and Hot Tub!

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)
"Great location--easy walk to downtown Frederick. Comfortable beds, pleasant spaces and light."
United States
Alan S.
The price is €216
includes taxes & fees
22 Jul - 23 Jul
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

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, (66 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 €286
includes taxes & fees
5 Jul - 6 Jul
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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 €291
includes taxes & fees
29 Jun - 30 Jun
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

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 €331
includes taxes & fees
14 Jul - 15 Jul
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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 €376
includes taxes & fees
30 Jun - 1 Jul
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 €369
includes taxes & fees
28 Jun - 29 Jun
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront

Harpers Ferry: Charming Home w/ Patio & Fireplace

Harpers Ferry: Charming Home w/ Patio & Fireplace
Harpers Ferry
10.0 out of 10, Exceptional, (10 reviews)
"Great location and amenities, super clean and the smores were a nice bonus "
United States
William S.
The price is €386
includes taxes & fees
29 Jun - 30 Jun
Harpers Ferry: Charming Home w/ Patio & Fireplace
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

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Shepherdstown Holiday Homes information

Number of reviews
591
Accommodation
333 Holiday Homes
Lowest Price
€216
Highest Price
€392