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Our top choices for Winchester vacation homes

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (25 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is AED 496
AED 801 total
includes taxes & fees
4 Jun - 5 Jun
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 AED 529
AED 1,114 total
includes taxes & fees
26 May - 27 May
Newly renovated Farm cottage with Mountain views

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 437
AED 1,247 total
includes taxes & fees
27 May - 28 May
Bluemont home just minutes to wineries, breweries, hiking and more!

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
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 647
AED 1,178 total
includes taxes & fees
1 Jun - 2 Jun
Mountain home w/ hot tub & sunroom

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is AED 419
AED 1,230 total
includes taxes & fees
27 May - 28 May
Greek Spa • Private Acreage • Stonefire pizza oven

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.
Cameron Charmer pristine downtown apt with double master suites

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 608
AED 1,458 total
includes taxes & fees
7 Jun - 8 Jun
Comfy Getaway in Strasburg, VA!

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
The price is AED 1,462
AED 2,503 total
includes taxes & fees
6 Jun - 7 Jun
4BR Golf Retreat • 3 Courses • Pool Table

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

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is AED 1,054
AED 2,067 total
includes taxes & fees
7 Jun - 8 Jun
Luxury Riverfront Home Getaway with Hot Tub

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"We had a great stay "
United States
Lauren O.
The price is AED 367
AED 1,492 total
includes taxes & fees
25 May - 26 May
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

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, (10 reviews)
"Great tiny home by the owner’s house. Beautiful area (but not super convenient to shopping or restaurants). I thought it was great."
United States
John Mark
The price is AED 327
AED 836 total
includes taxes & fees
25 May - 26 May
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is AED 496
AED 1,124 total
includes taxes & fees
25 May - 26 May
Leesburg Hideaway- King Bed + Private Backyard

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, (49 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AED 493
AED 1,241 total
includes taxes & fees
25 May - 26 May
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

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 463
AED 1,012 total
includes taxes & fees
1 Jun - 2 Jun
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

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 566
AED 1,459 total
includes taxes & fees
26 May - 27 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Harpers Ferry
9.8 out of 10, Exceptional, (109 reviews)
"Laura was extremely helpful as we sorted out what we needed. Amazing location near Harpers Ferry and tons of fun stuff to do right there within shouting distance of the property."
United States
Steve Y.
The price is AED 499
AED 1,908 total
includes taxes & fees
25 May - 26 May
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is AED 514
AED 1,696 total
includes taxes & fees
7 Jun - 8 Jun
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

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 traveler
The price is AED 359
AED 1,049 total
includes taxes & fees
27 May - 28 May
Luray Escape . Hot Tub . 15 Min to Skyline Drive

super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.4 out of 10, Exceptional, (14 reviews)
"Lovely setting in horse country with nice amenities "
United States
Christopher v.
The price is AED 643
AED 1,185 total
includes taxes & fees
25 May - 26 May
super cosy cottage with high speed internet!
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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