Holiday Homes in Winchester

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Our top choices for Winchester holiday homes

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is NZ$371
includes taxes & fees
6 May - 7 May
Mountain View Bungalow in Front Royal

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is NZ$514
includes taxes & fees
3 May - 4 May
Newly renovated Farm cottage with Mountain views

Cottage w/hot tub & lake dock

Cottage w/hot tub & lake dock
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is NZ$566
includes taxes & fees
7 May - 8 May
Cottage w/hot tub & lake dock

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is NZ$583
includes taxes & fees
3 May - 4 May
Cameron Charmer pristine downtown apt with double master suites

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Lovely home and great view. Host communication was fabulous. The welcome snacks, wine, and toiletries were very sweet. "
United States
Kathryn B.
The price is NZ$662
includes taxes & fees
5 May - 6 May
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is NZ$552
includes taxes & fees
12 May - 13 May
Bluemont home just minutes to wineries, breweries, hiking and more!

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is NZ$541
includes taxes & fees
5 May - 6 May
Comfy Getaway in Strasburg, VA!

Greek Spa on private acreage! Stonefire pizza oven

Greek Spa on private acreage! Stonefire pizza oven
Front Royal
The price is NZ$591
includes taxes & fees
19 May - 20 May
Greek Spa on private acreage! Stonefire pizza oven

Forest Haven: Trails, Stars & Serenity (Ravens’ Ridge)

Forest Haven: Trails, Stars & Serenity (Ravens’ Ridge)
Shenandoah Farms
The price is NZ$862
includes taxes & fees
3 May - 4 May
Forest Haven: Trails, Stars & Serenity (Ravens’ Ridge)

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is NZ$893
includes taxes & fees
5 May - 6 May
Luxury Riverfront Home Getaway with Hot Tub

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

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (11 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
The price is NZ$1,239
includes taxes & fees
3 May - 4 May
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
The price is NZ$700
includes taxes & fees
12 May - 13 May
Virginia Mirror Cabin

Armory Quarters B

Armory Quarters B
3.0 star property
Bolivar
The price is NZ$328
includes taxes & fees
3 May - 4 May
Armory Quarters B

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.6 out of 10, Exceptional, (8 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is NZ$373
includes taxes & fees
9 May - 10 May
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Luray
9.8 out of 10, Exceptional, (44 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is NZ$569
includes taxes & fees
3 May - 4 May
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Sunset Mountain Cabin

Sunset Mountain Cabin
Rileyville
9.8 out of 10, Exceptional, (38 reviews)
"Absolutely enjoyed our time here! So peaceful and beautiful! The host was amazing and very responsive! Loved the hot tub and how very open the space was. Definitely would come back!"
United States
Kim B.
The price is NZ$673
includes taxes & fees
5 May - 6 May
Sunset Mountain Cabin

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is NZ$671
includes taxes & fees
4 May - 5 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Luray Escape . Hot Tub . 15 Min to Skyline Drive

Luray Escape . Hot Tub . 15 Min to Skyline Drive
Luray
9.4 out of 10, Exceptional, (13 reviews)
"Such a cute place and just perfect!"
United States
Anonymous traveller
The price is NZ$490
includes taxes & fees
4 May - 5 May
Luray Escape . Hot Tub . 15 Min to Skyline Drive

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (23 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is NZ$436
includes taxes & fees
3 May - 4 May
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"The host was great in communicating check in and check out instructions! We appreciated being able to park in the driveway and the fenced in back yard was also a nice amenity. Would definitely stay here again!"
United States
Katherine s.
The price is NZ$519
includes taxes & fees
5 May - 6 May
Leesburg Hideaway- King Bed + Private Backyard
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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