
Holiday Homes in Winchester
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Our top choices for Winchester holiday homes

1. Cameron Charmer pristine downtown apt with double master suites
Cameron Charmer pristine downtown apt with double master suitesWinchester
9.8 out of 10, Exceptional, (11 reviews)
The price is AU$481
includes taxes & fees
13 Dec - 14 Dec

2. Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front RoyalFront Royal
10.0 out of 10, Exceptional, (51 reviews)
The price is AU$313
includes taxes & fees
24 Nov - 25 Nov

3. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6Front Royal
9.4 out of 10, Exceptional, (3 reviews)
The price is AU$558
includes taxes & fees
16 Nov - 17 Nov

4. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
NEW! Greek Spa - Frisbee Golf - Stonefire PizzaFront Royal
The price is AU$458
includes taxes & fees
13 Dec - 14 Dec

5. Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8
Trailside Retreat | Hot Tub + Sauna, Steps to Buzzard Rock | 4BR, Sleeps 8Front Royal
10.0 out of 10, Exceptional, (2 reviews)

6. Cozy 3BR Retreat | Perfect for Families & Groups
Cozy 3BR Retreat | Perfect for Families & GroupsApple Mountain Lake
The price is AU$453
includes taxes & fees
16 Nov - 17 Nov

7. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6Front Royal
The price is AU$559
includes taxes & fees
16 Nov - 17 Nov

8. Pool Table, Fireplace & Deck near Shenandoah Park
Pool Table, Fireplace & Deck near Shenandoah ParkFront Royal
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$706
includes taxes & fees
15 Nov - 16 Nov

9. Mountain Views w/Hot Tub, 95” TV & Trail Access
Mountain Views w/Hot Tub, 95” TV & Trail AccessShenandoah Farms
9.0 out of 10, Wonderful, (2 reviews)
The price is AU$668
includes taxes & fees
19 Nov - 20 Nov

10. Sunset Haven - 10 min from Skyline Drive. Hot Tub
Sunset Haven - 10 min from Skyline Drive. Hot TubFront Royal
9.6 out of 10, Exceptional, (8 reviews)

11. ⭐️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, (17 reviews)
The price is AU$998
includes taxes & fees
1 Dec - 2 Dec

12. Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Hidden Creekside retreat near 5 national parks, including Harpers FerryMartinsburg
10.0 out of 10, Exceptional, (14 reviews)
The price is AU$378
includes taxes & fees
14 Nov - 15 Nov

13. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Custom Train-Themed Lodge on 7 Private Acres with Walking TrailsMartinsburg
9.8 out of 10, Exceptional, (25 reviews)
The price is AU$369
includes taxes & fees
18 Nov - 19 Nov

14. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery
Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, WineryHarpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
The price is AU$418
includes taxes & fees
15 Nov - 16 Nov

16. Cozy house by the lake.
Cozy house by the lake.Wardensville
10.0 out of 10, Exceptional, (228 reviews)
The price is AU$476
includes taxes & fees
30 Nov - 1 Dec

17. Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Huckleberry Hills | Hot Tub & Fire Pit & DogsHarpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
The price is AU$699
includes taxes & fees
18 Nov - 19 Nov

18. 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, (10 reviews)
The price is AU$463
includes taxes & fees
1 Dec - 2 Dec

19. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WVBerkeley Springs
9.8 out of 10, Exceptional, (6 reviews)
The price is AU$475
includes taxes & fees
15 Nov - 16 Nov

20. Walk to Stores: Home in Historic Shepherdstown!
Walk to Stores: Home in Historic Shepherdstown!Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
The price is AU$527
includes taxes & fees
19 Nov - 20 Nov
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

Holiday Inn Winchester Se-Historic Gateway by IHG
10/10 Excellent

Days Inn by Wyndham Winchester
8/10 Good
Find out more about Winchester
Winchester Holiday Homes information
Number of reviews | 189 |
|---|---|
Accommodation | 729 Holiday Homes |
Lowest Price | AU$313 |
Highest Price | AU$998 |




























































