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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 656 Vacation Homes in Winchester with updated reviews, rates, and availability.

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Outdoor dining

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (199)
"My wife and I had a great time exploring the surrounding area and had a wonderful time relaxing in the cabin. It was very clean!"
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Property grounds

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (46)
"The location was perfect for outings in the area. "
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

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

9.8 out of 10, Exceptional, (97)
"We had great time fishing, canoeing and sightseeing. We visited Charles Town and went on the night time Ghost Tour. This area is loaded with Civil war history.The fish were hiding but the weather was perfect.Scott was a great host. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Outdoor spa tub

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (174)
"The highlight of the rental for us was definitely the property. We loved the view and our kids enjoyed wading in the river. Hot tub was great after days spent hiking in Shenandoah! "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Terrace/patio

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

10.0 out of 10, Exceptional, (31)
"We enjoyed a retreat from the city in this lovingly cared for farmhouse. Tom was super responsive and our kids had a great time playing in the creek and in the woods. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Lovely home, wonderful location.
Exterior

Lovely home, wonderful location.

10.0 out of 10, Exceptional, (64)
"Such a charming little house in a great location. Walking distance to restaurants and shops and short drive to the caverns. We really enjoyed our visit. The check in process was easy and the place was clean and inviting. Would definitely stay again. "
The price is AED 478
AED 995 total
includes taxes & fees
19 May - 20 May
Lovely home, wonderful location.
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

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

10.0 out of 10, Exceptional, (116)
"Jill was ver communicative and the home was well equipped. Couldn’t have been more ideal."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Secluded River Cabin Getaway (Masten Cabin)
Miscellaneous

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (147)
"We had a wonderful stay! Cabin was clean and welcoming, beautiful views, and overall a charming, relaxing cabin in the woods!"
Secluded River Cabin Getaway (Masten Cabin)
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (91)
"Great family stay! Highly recommend "
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (32)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (49)
"A great place to host family for an event. House has remarkable space and property was great to hang out or for the kids to run around. Host was super responsive. "
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

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

9.8 out of 10, Exceptional, (218)
"This is the first time I have ever seen Virginia so I booked this VRBO near all the things we wanted to do. Our stay was fantastic! Check in and check out was easy! We were able to communicate with the host who was so nice and very helpful! The house was clean, comfortable, and we didn’t want to leave at the end of our stay! I can’t say enough about the property and how peaceful it was. Our two German shepherds had the best time exploring and running through the creek with us! We enjoyed a cup...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (50)
"My husband, mother and I had a great stay at the Cottage on King. It’s tiny but we loved it. It’s beautifully decorated and you can’t get much better in terms of location. There were plenty of towels and other amenities to make for a comfortable stay. The beds and pillows were comfortable- not amazing but slept fairly well. You can hear the traffic but it didn’t bother us. "
The price is AED 441
AED 1,048 total
includes taxes & fees
5 May - 6 May
Cottage on King | Charming Historic Leesburg Home
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Aerial view

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

10.0 out of 10, Exceptional, (44)
"A home away from home! We had a fabulous stay - doing day hikes in the national park (Thornton Gap is an easy 30min drive) and spending family time cooking, playing games in the evenings. We appreciated all the nice details Diana arranged for our stay. So glad we chose this location! "
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (94)
"We used this beautiful home for a history trip of DC landmarks and regional Civil War Battlefields. The location was great. The drive into DC averaged about an hour and 45 minutes in the mornings due to traffic, but all the other Civil War destinations were much less and the house is large and very well maintained. The family loved sitting in the hot tub each night after a long day of walking and had the extra pleasure of a herd of deer that greeted us each night next along side the driveway...
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

9.8 out of 10, Exceptional, (179)
"We had such a wonderful time in this all accommodating, cozy, beautiful cabin! We caught trout in Paddy Creek that we brought back to the cabin and cooked for dinner. We hiked the trail behind the cabin through the national park. We relaxed!! A much needed getaway from the hustle and bustle!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Beautiful Log Chalet/Cabin with Hot Tub
Smart TV, fireplace, DVD player, computer

Beautiful Log Chalet/Cabin with Hot Tub

10.0 out of 10, Exceptional, (65)
"Stayed with a group of women for Berkeley springs spa weekend. We had a wonderful weekend, close to town and far enough away to enjoy the evening woods. The house was on a long dirt road, such a peaceful place and beautiful outdoor area with hot tub. Such a great place. "
Beautiful Log Chalet/Cabin with Hot Tub
The Lodge at Bear Rock
Smart TV, fireplace, video games, foosball

The Lodge at Bear Rock

The Lodge at Bear Rock
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (43)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub
Waterfront property in Harpers Ferry - Private River Access
Property grounds

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (24)
"Home was great and clean! Matt communicated well and was quick to respond to any questions. Loved being close by to historic Harper’s Ferry! Had a wonderful time at Antietam. Had numerous deer sightings close to the property in the evenings. Would definitely stay here again! A"
Waterfront property in Harpers Ferry - Private River Access
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
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Lovely cabin, very clean and well maintained. A girlfriend weekend and we wanted a great place to hang out and this fit the bill. We never got the TV to work but could be user error. "
The price is AED 1,062
AED 1,345 total
includes taxes & fees
7 May - 8 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
Star view cabin-Riverfront
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

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

9.8 out of 10, Exceptional, (97)
"We had great time fishing, canoeing and sightseeing. We visited Charles Town and went on the night time Ghost Tour. This area is loaded with Civil war history.The fish were hiding but the weather was perfect.Scott was a great host. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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.