Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (358)
"We had a wonderful stay at Deer Haven. The house was clean and very comfortable. The views were amazing, and the hot tub was perfect after long days of hiking. Nice outside deck seating and interior seats to allow for maximum views enjoyment! Would definitely rent this house again if we return to the area."
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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
30 Nov - 1 Dec
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!

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (204)
"This is three fifth time we’ve stayed here. It’s a gorgeous secluded area, so quiet and peaceful with no one around. Walk out the front door for hours on end of hiking. Great beds, great tv, fun pool table and three best porch! Will continue to return! Pet friendly too!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Secluded Mountain Cabin with Spectacular Views- Hiker's Dream

10.0 out of 10, Exceptional, (36)
"This was the most perfect place to stay. The entire home was incredibly clean and had everything we needed. The view is stunning, and the outlook was a perfect place to watch the sunrise. The host was very responsive and helpful. I would not have changed a single thing about this trip and we will definitely be back. "
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream

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.

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

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!

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 AU$702
includes taxes & fees
26 Nov - 27 Nov
NEW LISTING! Mountain Chic Retreat by RedAwning

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

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (154)
"We enjoyed our time at the cabin and the views are unbeatable"
The price is AU$527
includes taxes & fees
8 Dec - 9 Dec
Overlook Mountain Cabin

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit Kayaks & Tubes for Floating

9.2 out of 10, Wonderful, (22)
"Great spot for a group to explore Shenandoah and the Skyline/Blue ridge!"
The price is AU$1,161
includes taxes & fees
8 Dec - 9 Dec
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit Kayaks & Tubes for Floating

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (25)
"Perfect property for 5 adult women who love to have their own room! Plus each of us could have our own bathroom! Lots of good gathering space but plenty of places for solitude. Great hiking. Awesome stay"
White House Inn - Historic Home in Harpers Ferry!

‘Mountain Town Adventures’ Home w/ Fire Pit!

9.2 out of 10, Wonderful, (21)
"Quiet, relaxing and interesting roads to town. Each day was an adventure."
‘Mountain Town Adventures’ Home w/ Fire Pit!

Luxury secluded house by forest and river; hot tub; fast internet; kayak; tubes

10.0 out of 10, Exceptional, (21)
"We loved our weekend at this house! It’s quiet, pretty remote, and the view is incredible. I could have spent the entire weekend on the deck looking out over the mountains. Ashok was very kind and communicative, and their house is a great place for a getaway."
Luxury secluded house by forest and river; hot tub; fast internet; kayak; tubes

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

Big Sunny Family House

10.0 out of 10, Exceptional, (24)
"Clean house with lots of space! Well stocked with all the necessities and little added extras that made for a wonderful stay for girls weekend! There were 4 of us and we had more house than we needed but loved it because we all had our own bedroom. Owners are very responsive. We had no issues and will definitely be back! Walking distance to town with shopping, restaurants, and wineries.short drive to hiking trails and more wineries! "
Big Sunny Family House

Shenandoah Haven - Near Luray's Tourist Gems

9.2 out of 10, Wonderful, (7)
"This place was exactly like the pictures. Extras in the cupboards all details looked after. "
Shenandoah Haven - Near Luray's Tourist Gems

This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

9.2 out of 10, Wonderful, (5)
"This cabin was much larger than expected. It was clean and comfortable with two big bedrooms and two full (big!) bathrooms. Easy access to Winchester and cute cows!"
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

Surrounded by majestic trees Hilltop Hideaway is located within the woodlands.

9.8 out of 10, Exceptional, (81)
"Lovely time at the house with 7 girls. Clean, perfect for a group this size. Beautiful property. Easy to check in and out."
The price is AU$662
includes taxes & fees
26 Nov - 27 Nov
Surrounded by majestic trees Hilltop Hideaway is located within the woodlands.
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 Winchester

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is AU$592
includes taxes & fees
3 Dec - 4 Dec
Dreamtime - Modern A-frame Cabin w/ Hot tub

Secluded Pet-Friendly High-Tech Log Cabin in the Woods

9.6 out of 10, Exceptional, (165)
"I enjoyed every peaceful moment I was there! Living near, and working in a big city is loud and stressful. This was just what the Dr. ordered! Beautiful home in a beautiful setting with great amenities. Loved the lower level deck and propane fire pit that was ready to use! My older dog had a few problems traversing the steps but he loved being there as well!!! Already booked another stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods

Hidden Gem in the woods with hot tub

9.4 out of 10, Exceptional, (63)
"Great location, a little out of the way, but very relaxing. Great hot tub and fire pit. My family and I had an amazing time. "
Hidden Gem in the woods with hot tub
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

Black Friday: Members save 30%+

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