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Our top choices for Winchester vacation homes

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 AED 588
AED 1,179 total
includes taxes & fees
28 Apr - 29 Apr
Newly renovated Farm cottage with Mountain views

Mountain cottage w/hot tub & lake

Mountain cottage w/hot tub & lake
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 AED 703
AED 1,260 total
includes taxes & fees
28 Apr - 29 Apr
Mountain cottage w/hot tub & lake

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 AED 727
AED 1,244 total
includes taxes & fees
29 Apr - 30 Apr
Cameron Charmer pristine downtown apt with double master suites

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (22 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AED 496
AED 814 total
includes taxes & fees
11 May - 12 May
Mountain View Bungalow in Front Royal

🔥 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 AED 695
AED 1,443 total
includes taxes & fees
5 May - 6 May
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

The Apple Mountain House

The Apple Mountain House
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is AED 726
AED 1,724 total
includes taxes & fees
12 May - 13 May
The Apple Mountain House

Greek Spa on private acreage! Stonefire pizza oven

Greek Spa on private acreage! Stonefire pizza oven
Front Royal
The price is AED 584
AED 1,436 total
includes taxes & fees
11 May - 12 May
Greek Spa on private acreage! Stonefire pizza oven

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

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 808
AED 1,705 total
includes taxes & fees
11 May - 12 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 AED 512
AED 1,355 total
includes taxes & fees
10 May - 11 May
Comfy Getaway in Strasburg, VA!

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access
Front Royal
The price is AED 641
AED 1,643 total
includes taxes & fees
11 May - 12 May
The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
Luxury Riverfront Home Getaway with Hot Tub

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

Forest Haven: Trails, Stars & Serenity (Ravens’ Ridge)
Shenandoah Farms
The price is AED 651
AED 1,938 total
includes taxes & fees
11 May - 12 May
Forest Haven: Trails, Stars & Serenity (Ravens’ Ridge)

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
The price is AED 1,139
AED 1,316 total
includes taxes & fees
29 Apr - 30 Apr
Virginia Mirror Cabin

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
Luray
10.0 out of 10, Exceptional, (71 reviews)
"Amazing location and cute design. Would definitely stay here again. "
United States
Ashley
The price is AED 364
AED 877 total
includes taxes & fees
11 May - 12 May
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

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, (43 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AED 493
AED 1,229 total
includes taxes & fees
30 Apr - 1 May
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

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 AED 327
AED 816 total
includes taxes & fees
28 Apr - 29 Apr
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is AED 551
AED 1,431 total
includes taxes & fees
28 Apr - 29 Apr
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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 AED 707
AED 1,460 total
includes taxes & fees
28 Apr - 29 Apr
Sunset Mountain Cabin

Armory Quarters B

Armory Quarters B
3.0 star property
Bolivar
The price is AED 579
AED 766 total
includes taxes & fees
28 Apr - 29 Apr
Armory Quarters B

Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (85 reviews)
"Very cute house with lots of charm. Beds were comfortable. Host responded to messages quickly. "
United States
Nicole G.
The price is AED 430
AED 949 total
includes taxes & fees
5 May - 6 May
Historical home, walkable to many restaurants and shops.
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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