Search Vacation Homes in Shepherdstown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Shepherdstown vacation 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 ¥39,947
¥73,693 total
includes taxes & fees
May 14 - May 15
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, (126 reviews)
"The home was a great location to explore downtown Frederick. It had everything that we needed "
United States
David J.
The price is ¥15,562
¥41,156 total
includes taxes & fees
May 18 - May 19
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (88 reviews)
"Great location and very comfortable. Definitely will consider for future trips to this area."
United States
Jon E.
The price is ¥25,241
¥52,499 total
includes taxes & fees
May 25 - May 26
Luxury Condo In Downtown Frederick

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 ¥19,585
¥45,506 total
includes taxes & fees
May 20 - May 21
Charming "Cream of the Crop" Cape ~❤️of Middletown

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 beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is ¥19,585
¥44,676 total
includes taxes & fees
May 17 - May 18
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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 ¥22,719
¥27,404 total
includes taxes & fees
May 13 - May 14
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

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, (42 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 ¥21,011
¥45,690 total
includes taxes & fees
May 13 - May 14
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

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 ¥17,598
¥54,098 total
includes taxes & fees
May 13 - May 14
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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 ¥22,938
¥63,059 total
includes taxes & fees
May 13 - May 14
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

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, (4 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
The price is ¥8,931
¥43,062 total
includes taxes & fees
May 13 - May 14
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

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 ¥21,998
¥47,490 total
includes taxes & fees
May 31 - Jun 1
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

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

Riverview Retreat - Pool, Hot Tub, and Mtn Views!
Harpers Ferry
10.0 out of 10, Exceptional, (4 reviews)
"Had a fantastic time and everything was great! Highly recommend this spot for a vacation if you’re headed for Harper’s ferry."
United States
James A.
The price is ¥28,829
¥83,562 total
includes taxes & fees
May 17 - May 18
Riverview Retreat - Pool, Hot Tub, and Mtn Views!

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 ¥26,457
¥65,253 total
includes taxes & fees
May 13 - May 14
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

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 ¥43,087
¥71,249 total
includes taxes & fees
May 18 - May 19
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

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.
The price is ¥27,419
¥35,046 total
includes taxes & fees
May 19 - May 20
Light Horse Inn: Suite 1

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 ¥29,338
¥50,589 total
includes taxes & fees
Jun 9 - Jun 10
Enchanting Cottage, walk to Downtown Harpers Ferry

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 ¥24,129
¥57,803 total
includes taxes & fees
Jun 9 - Jun 10
Stone Cabin on Valley View: Fire Pit + Hot Tub

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 ¥18,077
¥68,023 total
includes taxes & fees
May 19 - May 20
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (107 reviews)
"The house was beyond expectations."
United States
Eddie J.
The price is ¥32,892
¥80,539 total
includes taxes & fees
May 15 - May 16
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

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, (61 reviews)
"Great location, spacious living area, plenty of linens, and excellent fire pit! "
United States
Maria Elena S.
The price is ¥28,061
¥52,498 total
includes taxes & fees
May 29 - May 30
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shepherdstown Hotel Reviews

Find out more about Shepherdstown

Shepherdstown Vacation Homes information

Number of reviews
846
Accommodation
308 Vacation Homes
Lowest Price
¥27,404
Highest Price
¥83,562