
Holiday Homes in Upperville
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Our top choices for Upperville holiday homes

1. 1910 Farmhouse on 6 Acres • VA Wine Country
1910 Farmhouse on 6 Acres • VA Wine CountryMarshall
9.6 out of 10, Exceptional, (5 reviews)
The price is AU$500
includes taxes & fees
1 Dec - 2 Dec

2. super cosy cottage with high speed internet!
super cosy cottage with high speed internet!Middleburg
9.6 out of 10, Exceptional, (19 reviews)
The price is AU$424
includes taxes & fees
1 Dec - 2 Dec

3. 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$551
includes taxes & fees
4 Nov - 5 Nov

4. Mountain home w/ hot tub & sunroom
Mountain home w/ hot tub & sunroomFront Royal
9.0 out of 10, Wonderful, (32 reviews)
The price is AU$444
includes taxes & fees
5 Nov - 6 Nov

5. Spacious Modern Home on Middleburg Horse Farm
Spacious Modern Home on Middleburg Horse FarmMiddleburg
10.0 out of 10, Exceptional, (22 reviews)
The price is AU$811
includes taxes & fees
4 Nov - 5 Nov

6. 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$689
includes taxes & fees
30 Nov - 1 Dec

7. Hunters Retreat with High Speed Internet
Hunters Retreat with High Speed InternetMiddleburg
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$1,213
includes taxes & fees
8 Nov - 9 Nov

8. The Blue Jay | New House in the Woods w/ Hot Tub
The Blue Jay | New House in the Woods w/ Hot TubHarpers Ferry
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$572
includes taxes & fees
5 Nov - 6 Nov

9. 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$360
includes taxes & fees
5 Nov - 6 Nov

10. Cozy 3BR Retreat | Perfect for Families & Groups
Cozy 3BR Retreat | Perfect for Families & GroupsApple Mountain Lake
The price is AU$476
includes taxes & fees
4 Nov - 5 Nov

11. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6Front Royal
10.0 out of 10, Exceptional, (1 review)
The price is AU$536
includes taxes & fees
8 Nov - 9 Nov

12. 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$627
includes taxes & fees
4 Nov - 5 Nov

13. Historic 6BR • EventsandConcierge! • Pool • Wineries
Historic 6BR • EventsandConcierge! • Pool • WineriesHume
The price is AU$1,698
includes taxes & fees
4 Nov - 5 Nov

14. Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front RoyalFront Royal
10.0 out of 10, Exceptional, (47 reviews)
The price is AU$292
includes taxes & fees
8 Nov - 9 Nov

15. 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, (9 reviews)
The price is AU$434
includes taxes & fees
2 Dec - 3 Dec

16. Still Meadow Farm
Still Meadow FarmPurcellville
10.0 out of 10, Exceptional, (2 reviews)
The price is AU$1,728
includes taxes & fees
9 Nov - 10 Nov

17. Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Iconic Chalet: Sauna • Hot Tub • Fire Pit • PlungeShannondale
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$681
includes taxes & fees
17 Nov - 18 Nov

18. Leesburg Hideaway- King Bed + Private Backyard
Leesburg Hideaway- King Bed + Private BackyardLeesburg
10.0 out of 10, Exceptional, (39 reviews)
The price is AU$421
includes taxes & fees
11 Nov - 12 Nov

19. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
NEW! Greek Spa - Frisbee Golf - Stonefire PizzaFront Royal
The price is AU$396
includes taxes & fees
30 Nov - 1 Dec

20. Stone Cabin on Valley View: Fire Pit + Hot Tub
Stone Cabin on Valley View: Fire Pit + Hot TubHarpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
The price is AU$553
includes taxes & fees
3 Dec - 4 Dec
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 Upperville Hotel Reviews

Travelodge by Wyndham Winchester
8/10 Good
Find out more about Upperville
Upperville Holiday Homes information
Number of reviews | 227 |
|---|---|
Accommodation | 253 Holiday Homes |
Lowest Price | AU$292 |
Highest Price | AU$1,728 |



































































