
Upperville Holiday Rentals
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Our top choices for Upperville holiday rentals

1. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
2. Lunar Loft, with mountain views
Lunar Loft, with mountain views
3. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
4. 18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
5. 1910 Farmhouse on 6 Acres • VA Wine Country
1910 Farmhouse on 6 Acres • VA Wine Country
6. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
7. Cozy A frame cabin in quaint Front Royal. Dog friendly
Cozy A frame cabin in quaint Front Royal. Dog friendly
8. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
9. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.
10. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries
11. Mountain home w/ hot tub & sunroom
Mountain home w/ hot tub & sunroom
12. Mountain Cabin Retreat | Hot Tub & Foosball |
Mountain Cabin Retreat | Hot Tub & Foosball |
13. Blue Mountain Cabin, secluded, perfect for couples, near main road
Blue Mountain Cabin, secluded, perfect for couples, near main road
14. Spacious Modern Home on Middleburg Horse Farm
Spacious Modern Home on Middleburg Horse Farm
15. The Foxwood Cabin | Hot Tub, Screened Porch, Grill
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
16. super cosy cottage with high speed internet!
super cosy cottage with high speed internet!
17. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive
18. Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
Far View Shenandoah | Hot Tub, Movie & Game Room, Valley Views | 3BR & Sleeps 6
19. Your Peaceful Getaway in the Blue Ridge.
Your Peaceful Getaway in the Blue Ridge.
20. Luxury Mountain Retreat w/ Valley Views, Hot Tub
Luxury Mountain Retreat w/ Valley Views, Hot TubFind holiday rentals that suit your style
Top Upperville Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester
Find out more about Upperville
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upperville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Upperville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Upperville. Seeing all the best attractions is bound to make you fall in love with Upperville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Upperville short-term rentals, that won’t be hard to do.



































































