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, (18 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is €400
includes taxes & fees
6 May - 7 May
Exclusive Wooded Chalet w Magnificent River Views

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (87 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is €282
includes taxes & fees
6 May - 7 May
Luxury Condo In Downtown 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, (62 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is €231
includes taxes & fees
7 May - 8 May
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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, (41 reviews)
"Wonderful place, great location, you can easily walk to Market street. Very quiet part of town. Kitchen well stocked, it was nice having a real coffee maker. Communication with host was excellent. Will definately stay again. "
United States
Thomas W.
The price is €243
includes taxes & fees
12 May - 13 May
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Chic, pets, walk to downtown

Chic, pets, walk to downtown
Frederick
10.0 out of 10, Exceptional, (16 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.
Chic, pets, walk to downtown

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 €247
includes taxes & fees
12 May - 13 May
Charming "Cream of the Crop" Cape ~❤️of Middletown

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 €153
includes taxes & fees
13 May - 14 May
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

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 €336
includes taxes & fees
6 May - 7 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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, (45 reviews)
"Property was spotless. Excellent communication. Location perfect-could walk to a winery and the battlefields of Antietam. Many extras- Latte machine. Outside area very comfortable with beautiful views. Dog friendly. Really enjoyed our stay. "
United States
Debby
The price is €290
includes taxes & fees
25 May - 26 May
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (69 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.
Terra Alta - Incredible River Views and Hot Tub!

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is €280
includes taxes & fees
6 May - 7 May
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

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)
"Host was helpful and everything was wonderful."
United States
Karen
The price is €341
includes taxes & fees
6 May - 7 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

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 €324
includes taxes & fees
6 May - 7 May
Stone Cabin on Valley View: Fire Pit + Hot Tub

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"The house was a great location for what we were lookin for, the kids loved the hot Tub and being able to explore"
United States
Bryan S.
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

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 €125
includes taxes & fees
6 May - 7 May
Fell like home one hour away from Washington DC private parking and patio

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 €387
includes taxes & fees
12 May - 13 May
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Chic Spacious Downtown Home - 5 Mins To Frederick Health Hospital & Fort Detrick

Chic Spacious Downtown Home - 5 Mins To Frederick Health Hospital & Fort Detrick
Downtown Frederick
9.4 out of 10, Exceptional, (3 reviews)
"Overall fantastic!"
United States
Lori M.
Chic Spacious Downtown Home - 5 Mins To Frederick Health Hospital & Fort Detrick

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (17 reviews)
"Great spot"
China
Clara
The price is €268
includes taxes & fees
11 May - 12 May
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

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 €371
includes taxes & fees
17 May - 18 May
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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, (8 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is €385
includes taxes & fees
12 May - 13 May
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
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

Find out more about Shepherdstown

Shepherdstown Holiday Homes information

Number of reviews
761
Accommodation
288 Holiday Homes
Lowest Price
€125
Highest Price
€400