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Vacation Homes in Winchester

Our top choices for Winchester vacation homes

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (381)
"House had all we needed! "
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, (192)
"The cabin is an absolute gem, located in the mountains but within easy reach of groceries, restaurants, hiking, fishing, etc. The stay was spacious, clean, tidy, had plenty of entertainment options, and communication was timely. Would not hesitate to book again. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (160)
"A beautiful home and property. This is a wonderful weekend getaway home. Modern and comfortable, but especially quiet!"
Secluded River Cabin Getaway (Masten Cabin)

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

10.0 out of 10, Exceptional, (128)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

8.8 out of 10, Excellent, (8)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Mountain View Bungalow in Front Royal

"Excelente propiedad "
The price is ¥22,041
¥35,163 total
includes taxes & fees
Sep 5 - Sep 6
Mountain View Bungalow in Front Royal

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

9.6 out of 10, Exceptional, (190)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

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

10.0 out of 10, Exceptional, (62)
"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is ¥22,084
¥46,857 total
includes taxes & fees
Sep 9 - Sep 10
Cottage on King | Charming Historic Leesburg Home

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is ¥14,694
¥59,517 total
includes taxes & fees
Sep 1 - Sep 2
Terra Alta - Incredible River Views and Hot Tub!

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"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

Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

9.8 out of 10, Exceptional, (31)
"Immaculate home and a few minutes from the Shanandoa Mts. Peaceful place!"
The price is ¥23,672
¥54,740 total
includes taxes & fees
Aug 31 - Sep 1
Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

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

9.8 out of 10, Exceptional, (232)
"This house was exactly what we were looking for. We wanted a nice, secluded getaway and that’s what we got."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (103)
"We stay at Yellowwood every year. It is on a quiet lane in the most picturesque part of Virginia (if not the country)!Also, Middleburg is just a short drive (or walk) away.We love Yellowwood!"
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Deer Trail Cabin ~ Mtn views ~ Firepit ~ Hiking

9.6 out of 10, Exceptional, (16)
"We had a fantastic time staying here. A perfect spot in the Mountains, 7 min commute to the main street. The house was ideal for 2 adults and 2 toddlers. We will absolutely book next time we head to the Mts. Thank you for having us :) "
Deer Trail Cabin ~ Mtn views ~ Firepit ~ Hiking

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (8)
"Great place and good location."
The price is ¥26,449
¥45,351 total
includes taxes & fees
Aug 28 - Aug 29
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

A unique mountaintop getaway overlooking Willow Croft Winery.

10.0 out of 10, Exceptional, (103)
"The perfect 3 bed/3.5 bath new build cabin for a get away with friends or family. We have nothing negative to say about this property. Our stay was Amazing."
The price is ¥46,286
¥87,945 total
includes taxes & fees
Sep 2 - Sep 3
A unique mountaintop getaway overlooking Willow Croft Winery.

Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

7.0 out of 10, Good, (2)
"My husband and I thoroughly enjoyed our 4-night stay (with our two dogs)! Perfect location; close to Bryce Resort for downhill mountain biking (or skiing in the winter) and lots of hiking trails in the area. House was clean and so was the hot tub. Saw lots of wildlife during our stay. No issue with hot water in the shower like a previous review mentioned. Host was easy to communicate with and quick to respond if we had any questions. Would definitely stay again when visiting the area! "
The price is ¥21,644
¥41,024 total
includes taxes & fees
Aug 25 - Aug 26
Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "
Breathtaking View with an Indoor Pool

Luxury Cabin Getaway in the Blue Ridge Mountains

The price is ¥102,858
¥254,621 total
includes taxes & fees
Aug 25 - Aug 26
Luxury Cabin Getaway in the Blue Ridge Mountains
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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Top Winchester Hotel Reviews