Holiday Homes in Winchester

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Featured Holiday Homes in Winchester

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

9.8 out of 10, Exceptional, (175)
"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had an excellent stay at Jill’s VRBO! The home was spacious and clean, perfect for a relaxing weekend away. The location also is ideal for going to wineries near Leesburg and Middleburg. And Jill was a very attentive host— she made sure that someone was there to remove the snow from the driveway and responded to any messages we sent promptly."
Trailside Retreat in breathtaking Western Loudoun

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (363)
"The house was nice. There was everything that we needed for our stay. The view from the deck was beautiful. The bed was comfortable. The fireplace and hot tub were great"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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

9.8 out of 10, Exceptional, (212)
"Stayed here with my partner during a long weekend. Unfortunately, shortly after we arrived, the weather took a turn and we could not complete our stay. We were beyond sad but will be back asap! Carla has been the most accommodating host ever!!!! She was very understanding and was willing to work with us during the snow storm. The cabin is absolutely gorgeous!!! The cabin was clean, has everything and anything you could possibly need and then some. Will definitely be returning customers. Couldn’t...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (28)
"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"
The price is AU$645
includes taxes & fees
20 Feb - 21 Feb
White House Inn - Historic Home in Harpers Ferry!

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

9.8 out of 10, Exceptional, (90)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"
Walk to Potomac River and downtown Harpers Ferry

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

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

10.0 out of 10, Exceptional, (111)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Secluded Mountain Cabin with Spectacular Views- Hiker's Dream

10.0 out of 10, Exceptional, (41)
"If you are looking for a mountain house with great views and privacy, this is a perfect fit. All around great experience and I’d like to visit again. "
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (33)
"Great house! Lots of room and cozy. Even saw some deer! Highly recommend!"
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

9.8 out of 10, Exceptional, (48)
"We got a chance to celebrate our family 40 years of marriage with our family and it was an absolute blast. The host was very detailed in his instructions about the property ensuring we had everything we needed throughout our stay.and available to ensure He did so in a timely manner throughout our stay. The kind women cleaning and preparing the home put in extra time and was so sweat and pleasant as we began our stay. In terms of the property, it was well was well equipped and clean and the beds...
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (48)
"Is there traffic/road noise? Yes. Can you walk to everything on King St? Also yes. Tradeoffs."
The price is AU$552
includes taxes & fees
5 Mar - 6 Mar
Cottage on King | Charming Historic Leesburg Home

River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

10.0 out of 10, Exceptional, (43)
"Beautiful cabin in a secluded area perfect for an escape from the hustle. Loved relaxing in the hot tub and sitting by the fire place. I would definitely recommend for a relaxing and recharging cabin experience. "
The price is AU$1,024
includes taxes & fees
8 Mar - 9 Mar
River Woods Retreat:10min to River, L2 EV, Hikes, 2 Fireplaces, Hottub, SP 10mi

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

10.0 out of 10, Exceptional, (22)
"Our group of seven was very, very comfortable there. It was nice to have two separate living areas one on the upper floor and one on the lower floor where one area could be the quieter area and the other area could be the louder area. Bedrooms were separate from the main living spaces on both the first floor and the basement which was very nice. Price per value was excellent, and whenever I return to the area, I will happily stay there again if it’s available!"
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

Riverfront Retreat

10.0 out of 10, Exceptional, (26)
"We made a great choice in choosing the Riverfront Retreat for our Thanksgiving celebration. The large dining table fit our group and its close proximity to the kitchen made serving and cleanup a breeze. One bedroom is set apart from the others which worked perfectly for one couple who ducked out at 5am to catch a flight out of Dulles (about an hours drive) without disturbing others in the group. We enjoyed hiking in Seven Bends State Park and even toured the Shenandoah Caverns (a short drive)....
Riverfront Retreat

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (66)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (93)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (71)
"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."
Rural Home, Hot Tub, Campfire, Hardwood Floors

Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry

9.8 out of 10, Exceptional, (19)
"Family and friends surprised my sister for her 40th birthday with a weekend getaway. Host was very responsive and gave great recommendations. House is in a great location, everything was within 15-20 minutes away. Easy check-in process and very clean. Thanks again. "
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
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

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (340)
"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had everything we needed. John was proactive in his approach, taking the time to discuss our needs and preferences before our stay. His thorough communication and attention to detail ensured that my...
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (304)
"Quiet and the hot tub was popular. Nice winter trip through Shen Nat Park, but no snowshoeing."
The price is AU$418
includes taxes & fees
20 Feb - 21 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (36)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
Dreamtime - Modern A-frame Cabin w/ 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.