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Compare 248 Vacation Homes in Shepherdstown with updated reviews, rates, and availability.

Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is $145
$221 total
includes taxes & fees
Jun 2 - Jun 3
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Interior
Lake House w/ Pool and King Bed, Fishing - Dogs OK
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay, really nice place we enjoyed seeing the water"
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Pool
Pool, Hot Tub, and Fun for all!
10.0 out of 10, Exceptional, (5)
"This was our second time traveling to the area and staying at this house. Great place to stay. House was clean, lots of room for multiple guests. Nice pool and hot tub in the yard. There’s also a nice covered outdoor patio with a TV for hanging out, outside. Owner is very responsive and good to deal with. I will definitely stay again when in the area."
The price is $349
$600 total
includes taxes & fees
May 28 - May 29
Pool, Hot Tub, and Fun for all!
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Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (93)
"We had a lovely stay in this beautiful Harpers Ferry home. It was so amazing to stay in the historical area and be close and able to walk to all the National Park sites. We were most attracted to that lovely porch and enjoyed our coffee there in the early morning, watching the town come to life. We also liked afternoons reading and napping there and an evening glass of wine after dinner. The kitchen was well stocked with everything we needed, the furniture and beds were very comfortable. We will...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (100)
"Perfect location in historic Middletown. Our daughter stayed over night to be our driver to graduations. She recommends a circulating fan for the basement bedroom! Apparently, we, at the age of 83, kept the house a little too warm!"
The price is $145
$307 total
includes taxes & fees
Jun 2 - Jun 3
Charming "Cream of the Crop" Cape ~❤️of Middletown
Smart TV, fireplace, table tennis, books
Hot Tub, Poker Table, River Access & Kayaks and Wineries
10.0 out of 10, Exceptional, (5)
"It was great. Nice property, awesome location. Very private"
The price is $152
$410 total
includes taxes & fees
May 28 - May 29
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Exterior
Union Street Carriage Quarters
10.0 out of 10, Exceptional, (21)
"This was our third stay here in a short period of time as our house gets renovated. We just love its coziness & cleanliness. Great communication with owners. Highly recommend!"
Union Street Carriage Quarters
Private kitchen
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (12)
"The home is beautiful! The owners did an amazing job to make us feel welcomed and at home. They provided us we unexpected amenities like coffee creamer, bottle water and even a bottle of wine. We greatly appreciated the free Netflix especially since ti rained during part of our stay. The location is ideal for our weekend adventures."
The price is $135
$287 total
includes taxes & fees
Jun 26 - Jun 27
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Smart TV
*Luxury Condo In Downtown Frederick*
9.6 out of 10, Exceptional, (41)
"Very historic town great property walking distance to everything"
The price is $200
$356 total
includes taxes & fees
May 28 - May 29
*Luxury Condo In Downtown Frederick*
Property grounds
Hollow Hideaway is nestled between peaceful mountains and star filled skies
10.0 out of 10, Exceptional, (14)
"We enjoyed our weekend in this very comfortable, well appointed home. We love a king size bed with quality sheets! The family room couch was great for lounging. We look forward to coming back!"
Hollow Hideaway is nestled between peaceful mountains and star filled skies
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Berryville Home: Walk to Main Street!
10.0 out of 10, Exceptional, (5)
"Great house, like brand new. Right around the corner from Main st which has nice coffee shops and a few eateries. Very nice place and location in Berryville for those visiting the valley or the mountains just across the Shenandoah River. Thanks"
Pet-Friendly Berryville Home: Walk to Main Street!
Fridge, microwave, stovetop, dishwasher
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (8)
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Property grounds
Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (44)
"Stayed here for work. Had 5 guys at the house. Plenty of room and great deck to hang out on."
Terra Alta - Incredible River Views and Hot Tub!
Terrace/patio
White House Inn - Historic Home in Harpers Ferry!
10.0 out of 10, Exceptional, (15)
"The house was so much more beautiful and bigger in person than I realized from photos! The location is such an easy walk down into town. The host checked in with me several times to make sure I was doing okay and didn't need anything. Would book again!"
The price is $356
$763 total
includes taxes & fees
Jun 13 - Jun 14
White House Inn - Historic Home in Harpers Ferry!
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
9.4 out of 10, Exceptional, (96)
"A perfect location in Frederick. The Carroll Creek Canal is right behind the house and is beautifull! Aaron gave us excellent recommendations as to where to visit and eat. The house is older but clean, tidy and comfortable. We did use the kitchen to cook and gave Aaron a few pointers to improve what he had for utensils. Overall, I would come back again. Thanks Aaron"
The price is $140
$314 total
includes taxes & fees
Jun 2 - Jun 3
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Smart TV
The Penny Postcard Historic House
10.0 out of 10, Exceptional, (8)
"This is a spacious, comfortable home. Walking distance to dining, wine and convenience store. A bit far to downtown Harpers Ferry, but doable. We brought our own grill for outdoor cooking. Amy was super responsive to all my questions prior to our trip. I'd recommend this location to friends and family if ever in the area."
The Penny Postcard Historic House
Property grounds
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
8.8 out of 10, Excellent, (3)
"Comfortable stay. Has everything you need and more. Great backyard with swing-set, fire pit. Incredible sunset views overlooking the Potomac. Close to Harper’s Ferry, AT, Antietam, Boonsboro, C&O, walking, hiking, etc…"
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
Interior
*In The Heart Of Antietam*
9.6 out of 10, Exceptional, (73)
"This is a very solid VRBO. Pros: - Location is excellent; right in the downtown Sharpsburg next to a yummy ice cream place. It's easy to drive to and from. - Parking was good. There's a public lot across the street (no overnight there) and street parking in front of the unit. - There's a good amount of space in this unit with three bedrooms, a living room, dinning room, and kitchen. - The wifi is blazing fast; I was getting over 300 mbps when running speed tests. - It was a comfortable stay....
*In The Heart Of Antietam*
Fridge, microwave, oven, stovetop
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
10.0 out of 10, Exceptional, (46)
"Great little place to stay in Frederick for a couple or small family. House was clean and up to date with good Wi-Fi and well set up kitchen. Best part was being able to walk into the center of town for shops and restaurants in 5 minutes! Highly recommended!!"
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>
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See all available properties in Shepherdstown
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.

Other property types in Shepherdstown

Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is $75
$144 total
includes taxes & fees
Jun 9 - Jun 10
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, (18)
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is $94
$216 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Cottage
Property grounds
Plum Lazy on the Potomac
9.4 out of 10, Exceptional, (20)
"My friends and I loved this house can’t wait to go back."
Plum Lazy on the Potomac
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.

Shepherdstown Vacation Homes information

Number of reviews
652
Accommodation
248 Vacation Homes
Lowest Price
$135
Highest Price
$356

Recent reviews of Shepherdstown hotels
Expedia verified reviews