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Vacation Homes in Winchester

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

9.8 out of 10, Exceptional, (206)
"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

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (156)
"It was clean. It had a beautiful drive to it and it was tucked up in the woods. It would be nice if there was curtains, but that is OK. You are surrounded by trees. Enjoyed our visit. Has a very cute town nearby. Wasn’t in the house very much was enjoying all the scenery."
Secluded River Cabin Getaway (Masten Cabin)

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

10.0 out of 10, Exceptional, (125)
"The view from the porch, accessibility to food, good coffee, hikes, shops, and important history, are unmatched. Our hosts are kind and accommodating. This is our second time here and won't be our last. "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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 AED 560
AED 1,215 total
includes taxes & fees
22 Jul - 23 Jul
Cottage on King | Charming Historic Leesburg Home

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

9.8 out of 10, Exceptional, (26)
"Immaculate home and a few minutes from the Shanandoa Mts. Peaceful place!"
The price is AED 592
AED 1,377 total
includes taxes & fees
22 Jul - 23 Jul
Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

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

9.6 out of 10, Exceptional, (185)
"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

Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

10.0 out of 10, Exceptional, (1)
"Our stay at Bala’s home was wonderful. The location right on the river is perfect for a relaxing getaway. A very close drive to the National Park and Front Royal. The home is updated nicely and amenities are well stocked, above average kitchen supplies from the typical vacation rental. Do note that there are no tvs in the bedrooms which we appreciated but some may not. Overall it was great. "
Rivers Edge Retreat with spectacular water views, Full kitchen, Games, Fishing

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (136)
"Wonderful house for a great weekend away"
The price is AED 845
AED 1,621 total
includes taxes & fees
10 Aug - 11 Aug
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (118)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

Shenandoah Riverfront Retreat! Fun for the whole family!

10.0 out of 10, Exceptional, (16)
"This property was perfect for our family!! Great communication from the owner. Would stay again!! "
Shenandoah Riverfront Retreat! Fun for the whole family!

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 AED 732
AED 2,192 total
includes taxes & fees
27 Jul - 28 Jul
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (255)
"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

The Blue Pearl by Zen Living

10.0 out of 10, Exceptional, (3)
"We stayed at the Blue Pearl during a long weekend trip with our family of four and our dog. The house and property are beautiful! We had all the amenities we needed during our stay, and loved the fenced in backyard and hot tub. The beds were very comfortable. The location was ideal-walking distance to shops and restaurants and a short 5 minute drive to Luray Caverns. We enjoyed pizza from the Italian restaurant around the corner on our first night. Our family is looking forward to our next...
The Blue Pearl by Zen Living

Lake House w/ Pool and King Bed, Fishing - Dogs OK

9.4 out of 10, Exceptional, (22)
"The lake house property was clean, comfortable and was an excellent location. We enjoyed the proximity to Gettysburg, Harper’s Ferry, Cacapon State Park and the C and O Towpath bike trail and museum."
Lake House w/ Pool and King Bed, Fishing - Dogs OK

Secluded Mountain Retreat with Stunning Views, Hot Tub, Wifi and more

9.8 out of 10, Exceptional, (31)
"My husband and I stayed at the property for our anniversary. It was the perfect spot to get away from the city, unplug, and unwind. The owner is incredibly responsive. Check-in was a breeze. The property is exactly as described/ pictured. We’re already planning another trip."
Secluded Mountain Retreat with Stunning Views, Hot Tub, Wifi and more

Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

9.8 out of 10, Exceptional, (53)
"Great place for our college friends to fish & enjoy nature (& have a laugh or 2)"
Breathtaking! 5 Acre Private Riverfront Cabin in the Mountains!

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

9.8 out of 10, Exceptional, (228)
"Beautiful home"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (90)
"Loved the view, such a relaxing weekend. Hist was very responsive and access was a breeze. Highly recommend "
The price is AED 661
AED 1,567 total
includes taxes & fees
30 Jul - 31 Jul
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

9.8 out of 10, Exceptional, (6)
"The property is beautiful and just outside of Front Royal. We visited local vineyards and hit the skyline drive on the way home. We loved relaxing in the GeoDome home!"
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres 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.
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Top Winchester Hotel Reviews