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Compare 245 Vacation Homes in Shepherdstown with updated reviews, rates, and availability.

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AED 533
AED 817 total
includes taxes & fees
24 Nov - 25 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

9.8 out of 10, Exceptional, (118)
"The property was just as it was pictured online. We appreciated how clean and orderly it was. Plenty of space and just a short walk into town and to hiking trails."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Pet-Friendly Berryville Home: Walk to Main Street!

9.2 out of 10, Wonderful, (12)
"The house was lovely and we wanted for nothing. I only want to report that the sink in the bathroom did not drain very well. Other suggestions, the bath tub should have better anti- slip coverage or a different product. Please include instructions on how to regulate the heat / air conditioner. "
Pet-Friendly Berryville Home: Walk to Main Street!

Newly constructed 6 bedroom home

10.0 out of 10, Exceptional, (4)
"This new home is beautiful, clean, and well-equipped. The beds were comfortable. Great neighborhood for walks, still under construction right across the street. Host was quick to respond to inquiries. We were surprised to discover that there is a family living in the basement, as we thought we had rented the entire home. Apparently, it is disclosed on the website if you click on "See all rooms and bed details" and look under the 3 bathrooms section that the basement is not part of the...
The price is AED 680
AED 1,589 total
includes taxes & fees
24 Nov - 25 Nov
Newly constructed 6 bedroom home

NEW LISTING! Mountain Chic Retreat by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (1)
"I grew up in Jeff Co, but never explored this area of the county. Great house very peaceful! Only feedback and down side was NO laundry machines on site. "
The price is AED 555
AED 1,657 total
includes taxes & fees
24 Nov - 25 Nov
NEW LISTING! Mountain Chic Retreat by RedAwning

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (25)
"Honestly, it was exactly how it was described - which was great!"
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, (103)
"comfortable, clean and charming townhouse in the heart of downtown Frederick. I especially liked the decor (including a pac man that really works!) and the landscaped outdoor area with seating. "
The price is AED 514
AED 1,152 total
includes taxes & fees
22 Dec - 23 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.8 out of 10, Exceptional, (171)
"Wonderful home close to many attractions in western Maryland.It’s any easy drive into Harper’s Ferry, Sherpardstown, and it’s walking distance to the battlefield of Antietam. Check out Little Brick Coffee in the morning and if you enjoy wine visit Antietam Creek Winery. The house itself was like a trip to past with all the modern conveniences.It was very clean and despite being in town it was also very quiet. Thanks, we’ll definitely be back!"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Hillside Hideaway in Lowertown Harpers Ferry

9.8 out of 10, Exceptional, (10)
"The house was great, beds were comfy, everything we wanted to see was close by so we could walk, and despite being close to everything it was still quite private. "
Hillside Hideaway in Lowertown Harpers Ferry

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

10.0 out of 10, Exceptional, (25)
"Our family met here for a weekend getaway. The house is amazing and is stocked with everything you need! The pool room is great, the patio out back has firepits for you to sit around at night, and the kids enjoyed riding their bikes on the property and at the park. The views are beautiful and the beds were comfortable.We brought most of our food with us, but there are stores about 15 minutes away. Its a perfect spot to unplug and relax. "
The price is AED 1,653
AED 3,148 total
includes taxes & fees
3 Dec - 4 Dec
4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acres retreat, next to Park

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (9)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area

Charles Town Townhome: 9 Mi to Harpers Ferry

10.0 out of 10, Exceptional, (8)
"I spent a week in the property and thoroughly enjoyed my stay. The check-in process was very smooth and the home is immediately welcoming. The downstairs is modern and spacious. It is a very family friendly place that is equally suited for single or couple travelers. I love the intentionality of blending a play nook for kids into a gathering area for adults. The upstairs is very comfortable. The master bedroom features a king beg that seemingly hugs you while you sleep. The en suite bath...
Charles Town Townhome: 9 Mi to Harpers Ferry

SKI YA LATER Whitetail

9.8 out of 10, Exceptional, (7)
"My family and I Stayed at Ski Ya Later this weekend. Pros: Great location directly next to Whitetail Ski resort and a short drive to the town of Mercersburg. The beds are very comfortable. The place is modern, decorated very nicely. Check in was a breeze. Nice TV, Chargers galore. Spacious- there were four of us (2 adults , 2 teens) but the place can easily sleep up to 8. Cons: We we’re very disappointed with the lack of cleanliness / cleaning service that occurred prior to our visit. I took...
SKI YA LATER Whitetail

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

10.0 out of 10, Exceptional, (1)
"Nice and clean, easy check in and out. The unit was easy to get to, the neighborhood was quiet and it was easy to get to the highway. We were on our way to Ocean City and needed a stop over in MD. This was a pleasant location, easy to get to and perfect for a one night stop over. It was very clean and neat and the off street parking spot was a nice convenience."
The price is AED 331
AED 705 total
includes taxes & fees
24 Nov - 25 Nov
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (21)
"Our stay at this vacation home was very enjoyable! The house was clean, well maintained and comfortable. It is located on a nice piece of property with a beautiful view of the Shenandoah River. The owner provided a lot of necessities like bed sheets, bath towels, soap, shampoo and even coffee supplies. The house is up to date and has a nice basement entertainment area. The fire pit area near the river was probably our favorite amenity. We enjoyed it on a couple evenings while enjoying the...
Waterfront property in Harpers Ferry - Private River Access

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is AED 511
AED 1,678 total
includes taxes & fees
5 Dec - 6 Dec
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (29)
"Overall was beautiful. Very easy to communicate with the owner. The view was breathtaking. I’d definitely recommend this to my other families and friends. Thanks again for making our stay so pleasant. "
Modern Country House on the Shenandoah River

Woods Song - Natures Promise

9.8 out of 10, Exceptional, (32)
"This location was a nice place to stay. Definitely quiet and off the beaten track. We generally stay closer in to Berkeley Springs, but decided this time to go further out of town. The place was very clean and the hot tub was very well maintained. The appliances, as expected, were dated but worked fine. The only potential downside was that there were two other properties right behind this one. In the spring or summer with the trees in full foliage it would be very private. In the late fall a...
Woods Song - Natures Promise

Hot Tub, Poker Table, River Access & Kayaks and Wineries

9.6 out of 10, Exceptional, (17)
"I stayed with some friends in the house and we had a great time, the beds were comfortable, the house was clean, the outside was quiet and private. We didn’t use the hot tub or the fire pit, but we played cards on the table outside and all in all had a great time."
The price is AED 573
AED 1,522 total
includes taxes & fees
3 Dec - 4 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries
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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Other property types in Shepherdstown

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"My husband and I stayed here to celebrate our second anniversary. We wanted just a quiet getaway and it was the perfect place. Definitely will have to come back again."
The price is AED 162
AED 403 total
includes taxes & fees
3 Dec - 4 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Welcome to this patch of serenity on the river's edge, to this hideaway.

9.8 out of 10, Exceptional, (60)
"Loved everything. Quiet, peaceful….loved the small deck off the upstairs bedroom."
Welcome to this patch of serenity on the river's edge, to this hideaway.

Plum Lazy on the Potomac

9.2 out of 10, Wonderful, (23)
"Quiet and relaxing. Had hoped to get the kayaks out but one girl was just post surgery on her wrist so we had to bypass them this trip. Our favorite part of the weekend was sitting on the porch and looking at the Potomac. So relaxing. The house was cute and clean, just like the pictures. Shopped in Shepersdstown and ate at the Blur Moon. It was fun!! Could not find parking in Harper’s Ferry. We were bummed about that but it didn’t ruin our weekend. We will be back to kayak and swim. "
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.