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Vacation Homes in Winchester

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (152)
"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)

The Blue Pearl by Zen Living

10.0 out of 10, Exceptional, (2)
"This space is just the right fit for our small family of three. The decor strikes a balance—simple yet striking. As someone who prefers cooler shades over warm tones, with a fondness for lavender, olive, and navy, I truly felt at home here. We can't wait for our next visit. This will definitely be our top choice for accommodations in Luray."
The price is SAR 394
SAR 1,112 total
includes taxes & fees
17 Jun - 18 Jun
The Blue Pearl by Zen Living

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

10.0 out of 10, Exceptional, (122)
"My husband and I thoroughly enjoyed staying in Harper's Ferry. It is a beautiful historic town with many sights to see. This house made it very convenient to have quick access to everything. It was especially useful for time management. We were able to complete our full itinerary that we had planned in advance."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (372)
"My family and I enjoyed our week in the Shenandoah Valley. This property had everything we needed to enjoy meals together and quality family time in the evening. There was so much to do in the area. We would definitely love to visit again "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

A private home in Bolivar with a hot tub and yard. Pet friendly!

10.0 out of 10, Exceptional, (4)
"The house was cute and just the right size for us. It was close to everything we wanted to see and do"
A private home in Bolivar with a hot tub and yard. Pet friendly!

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

9.6 out of 10, Exceptional, (180)
"Will be back "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

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

9.8 out of 10, Exceptional, (104)
"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!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is SAR 647
SAR 1,340 total
includes taxes & fees
7 Jul - 8 Jul
Cottage on King | Charming Historic Leesburg Home

Cozy Lakeside Homestead

10.0 out of 10, Exceptional, (192)
"My wife and I loved our stay at this location. Was a perfect weekend getaway. We really enjoyed what the house had to offer, especially the hot tub, sauna, and fireplace. Made the cold rainy weather we had cozy and enjoyable as we huddled up inside. "
Cozy Lakeside Homestead

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

9.8 out of 10, Exceptional, (96)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
The price is SAR 2,211
SAR 4,094 total
includes taxes & fees
3 Jul - 4 Jul
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (29)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is SAR 601
SAR 1,213 total
includes taxes & fees
18 Jun - 19 Jun
Newly renovated Farm cottage with Mountain views

Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

10.0 out of 10, Exceptional, (6)
Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

River Perch on the Cacapon: private home on 27 acres and 1200 ft of riverfront

10.0 out of 10, Exceptional, (32)
"House was clean, nicely decorated and perfectly located in a quiet natural setting along the river. Really enjoyed our time here."
River Perch on the Cacapon: private home on 27 acres and 1200 ft of riverfront

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (11)
"Great place, very relaxing"
Cozy Country Getaway in the Heart of Upperville

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

4.0 out of 10, (1)
"Tony was our host. We never saw him. Nor did we get sheets for the bed we slept in. The hot tub was disgusting and appeared to have soap suds in it. There were no bowls in the kitchen. The upstairs shower had only hot water. The downstairs shower had only cold water. There was inadequate seating in the living room for the number of occupants staying there."
The price is SAR 553
SAR 1,044 total
includes taxes & fees
17 Jun - 18 Jun
Hot Tub, Fire Pit, Grill, Screened Porch & WiFi

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (17)
"We had a great time "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

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

10.0 out of 10, Exceptional, (50)
"A spacious and very nice home located in a great location - walking distance to the best brewery and the best bakery in the area. Looking forward to visiting again soon! "
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

10.0 out of 10, Exceptional, (8)
"Came to this cozy space for a long weekend getaway and had a really lovely time. Even in the cold and we got to enjoy the covered patio and watch a movie while snuggling up with all the blankets provided. While we were her we got a snow storm so we mainly stayed indoors, although we did venture into the hot tub one of the nights. Overall, we had a really nice stay and I look forward to returning. "
The price is SAR 584
SAR 1,383 total
includes taxes & fees
23 Jun - 24 Jun
Cozy mountain retreat minutes to the river, Luray, and 25 to Shenandoah NP!

Historic Slate Hill School House in Fort Valley, Virginia

10.0 out of 10, Exceptional, (112)
"Visiting family for Easter, this spot was close enough but also allowed us our own time with family"
Historic Slate Hill School House in Fort Valley, Virginia

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

10.0 out of 10, Exceptional, (14)
"location was close to the sites I wanted to see"
The price is SAR 503
SAR 1,251 total
includes taxes & fees
30 Jun - 1 Jul
Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!
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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