Holiday Homes in Shepherdstown

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Featured Holiday Homes in Shepherdstown

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!

Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

10.0 out of 10, Exceptional, (60)
"Clean cozy row home. Easy walk to downtown attractions. House gave excellent recommendations for food and things to see. Would definitely stay again at this property "
Walk to the canal and downtown!!! Cozy 1880 Fully Renovated townhome<br>

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 AU$346
includes taxes & fees
1 Dec - 2 Dec
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

800' of Glorious Shenandoah River frontage + 18 Private Acres

10.0 out of 10, Exceptional, (6)
"This property was awesome! Clean, nicely furnished, extra supplies if needed and a great layout. Two firepits were such a bonus. One by the house and one by the river. We will be returning!"
800' of Glorious Shenandoah River frontage + 18 Private Acres

Riverside Retreat Sum

10.0 out of 10, Exceptional, (1)
"Just the place we were looking for relaxing and cozy. Very nice property. "
The price is AU$315
includes taxes & fees
30 Nov - 1 Dec
Riverside Retreat Sum

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (36)
"Beautiful home. Nice location Enjoyed our stay very much"
Trailside Retreat in breathtaking Western Loudoun

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (121)
"We had a great time and loved your house."
Gorgeous 1840 Log Cabin- Downtown

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

9.6 out of 10, Exceptional, (17)
"My extended family met in Harper’s Ferry for a hiking weekend, and this was a perfect home base! Enough room for 8 of us plus dogs, and a beautiful outdoor space. We will definitely be back!"
The price is AU$646
includes taxes & fees
3 Dec - 4 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries

“The Train Depot” 2nd oldest in the US

10.0 out of 10, Exceptional, (73)
"The house is clean and well stocked. It's a great place to stay if spending a few days in Frederick, MD. "
“The Train Depot” 2nd oldest in the US

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (25)
"Great location in a very safe neighborhood! House was very roomy with very comfy beds. Would definitely stay here again!! "
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)
"We loved the historic home and its proximity to Carroll Creek and shopping! We were in town for a wedding and were able to walk everywhere we needed to go. "
The price is AU$521
includes taxes & fees
3 Dec - 4 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Enchanting Cottage, walk to Downtown Harpers Ferry

10.0 out of 10, Exceptional, (33)
"The cottage was very quaint. Peaceful. Walked to Harper's Ferry. Did some hiking. When into Charles Town to antique shop. Went to the Harper's Ferry Brewery."
The price is AU$515
includes taxes & fees
3 Dec - 4 Dec
Enchanting Cottage, walk to Downtown Harpers Ferry

ENTIRE 2 BDRM 2.5 BATH Duplex - Mountains, Rivers, Wineries, Breweries, Casino

9.4 out of 10, Exceptional, (135)
"My family enjoyed the spacious, comfortnabel and q house and close proximity to everything harper's Ferry has too offer,"
ENTIRE 2 BDRM 2.5 BATH Duplex - Mountains, Rivers, Wineries, Breweries, Casino

Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

10.0 out of 10, Exceptional, (9)
"Clean and welcoming home. No complaints."
Homey 'Ridgetop Retreat' - Walk to Hiking & Biking

Hollow Hideaway is perfect for your holiday stay!

10.0 out of 10, Exceptional, (30)
"We spent two nights at the home. It was exactly what we needed. The home was immaculate. The beds and linens were luxurious. There was a cute amenities kit in each bedroom - such a nice, extra touch. The home is off of the beaten path so very peaceful. The gas firepit on the covered porch was perfect since we could not use the wood firepit due to drought. The decor was tasteful and restful. The kitchen was well stocked. . We were happy to meet sweet Ellie. She joined us a few times during our...
Hollow Hideaway is perfect for your holiday stay!

A-Frame Mountain Retreat

10.0 out of 10, Exceptional, (19)
"This property is absolutely beautiful. Accurate to listing and very clean. Property is very private. We enjoyed a weekend away and it was so relaxing and worst it. We would definitely book again in the future. "
A-Frame Mountain Retreat

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!

Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay. Walking distance to restaurants and attractions. House had all necessary amenities and very clean!"
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Rare Find! Boutique Style Townhouse on the Creek!

10.0 out of 10, Exceptional, (19)
"We had a great stay at Ashley and Richard's townhouse. Beautifully renovated while maintaining the original charm. Location could not be better, right off the creek promenade with all the restaurants and shops in the historic downtown area just a short walk away. Don't forget to enjoy a stroll in beautiful Baker Park. The house was nicely decorated and very comfortable. The kitchen was well stocked with pots, pans, etc, allowing us to cook a few meals during our stay. Several nights we...
Rare Find! Boutique Style Townhouse on the Creek!

Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

8.6 out of 10, Excellent, (4)
"Home differed slightly from photos rugs were not included and house paint colors are different than what's listed on VRBO. Great scenery and wildlife views. Some small issues with cleanliness in the bathroom upon arrival. Noisy neighborhood (dogs barking, lots of loud trucks and 4-wheelers tearing up the gravel road outside). Grooves in gravel road + driveway not easy for a small car or sedan to get through. I would recommend outdoor lighting by the porch entry. Was difficult to navigate walking...
The price is AU$448
includes taxes & fees
3 Dec - 4 Dec
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly
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)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is AU$172
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.