Photo by KM Moore

Holiday Homes in Berryville

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Featured Holiday Homes in Berryville

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!

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

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (36)
"Wonderful place!!!"
Trailside Retreat in breathtaking Western Loudoun

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (20)
"What a wonderful stay! This VRBO was perfectly clean and super homey. We loved the decor and welcoming touches. I stayed with my colleagues for a week of offsite meetings, so we appreciated the many bedrooms and bathrooms plus the open meeting space. The wifi was a bit slow at times for our purposes working remotely. I'm sure a more casual user wouldn't have any issues. The location was fantastic. So peaceful and secluded feeling, but in reality just a short drive to Purcellville and Leesburg....
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

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$647
includes taxes & fees
2 Dec - 3 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (25)
"Hiking, playing in the creek, S'mores by the fire pit, enjoying meals on the porch all add up to fun memories. We enjoyed our stay. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (87)
"This was our third time staying at this beautiful property for our strategic planning session, and once again, it was a fantastic experience. The house is always spotless, spacious, and beautifully decorated, making it feel like a true home away from home. The host provided delicious meals throughout our stay, which added an extra level of convenience and enjoyment. Each meal was thoughtfully prepared and absolutely delicious—perfect for keeping our team energized and focused. The peaceful...
Gruner Bungalow at Otium Cellars

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!! "
The price is AU$1,477
includes taxes & fees
30 Dec - 31 Dec
White House Inn - Historic Home in Harpers Ferry!

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$466
includes taxes & fees
2 Dec - 3 Dec
Enchanting Cottage, walk to Downtown Harpers Ferry

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (44)
"Perfect. No complaints at all. Thank you again. "
The price is AU$469
includes taxes & fees
3 Dec - 4 Dec
Cottage on King | Charming Historic Leesburg Home

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

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!

Townhome in Leesburg Historic District!

10.0 out of 10, Exceptional, (18)
"Lovely property and well appointed. Close to bars and restaurants and lovely outside area"
Townhome in Leesburg Historic District!

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!

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$434
includes taxes & fees
3 Dec - 4 Dec
Harpers Ferry Cottage: Hot Tub, WiFi, Dog-Friendly

A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

10.0 out of 10, Exceptional, (1)
"Raisa's place was quaint and more than adequate. It was neat and had many interesting plants throughout the house. The backyard was great to have (especially being pet friendly). Access to Harper's Ferry was close by and very convenient. Recommend!"
A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (5)
"The cottage was just perfect for a short Girls Weekend trip. Jennifer and Federico were great communicators and responded quickly to any questions we had. The cottage is decorated nicely with lovely touches throughout. Comfortable beds. Loved the back yard. We sat in the Adirondacks most evenings and watched the deer graze! The location is wonderful for visiting Middleburg, Purcellville, Marshall and The Plains. Many wineries, breweries, shopping and good restaurants. And the mountain scenery...
Cozy Country Getaway in the Heart of Upperville
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 Berryville

13 BR Boutique in Berryville

7.4 out of 10, Good, (6)
"This house is a gem in progress. It was very spacious and naturally divided into separate areas so it worked well to group families with small children away from older couples without children. Several issues did develop during our stay which were immediately addressed. The dish washer was repaired and worked fine for us. The large common area had very minimal lighting but we moved lamps into the area to remedy that. There was ample refrigerator space but no freezer so we improvised with ice...
13 BR Boutique in Berryville

Stunning Former Winery w/ Pool & Mtn Views!

9.4 out of 10, Exceptional, (9)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
Stunning Former Winery w/ Pool & Mtn Views!

❤️ 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
10 Dec - 11 Dec
❤️ Secluded 1940s Romantic Tiny House on the River
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.