Photo by Michael Gibson

Upperville Holiday Rentals

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Check prices for these dates

Tonight
12 Jan - 13 Jan
Tomorrow
13 Jan - 14 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Upperville holiday rentals

Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
The price is S$2,352
includes taxes & fees
13 Jan - 14 Jan
'thomson Farm' Classic Home < 10 Mi to Vineyards!
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Staff was absolutely wonderful. Hotel was verybeasy to work with the entire time. I would recommend this place."
Michael 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Winchester

Frequently asked questions

Can I find a holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

How many holiday rentals are there in Upperville?

Choose from 5 Expedia holiday rentals in Upperville for a memorable holiday.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Dinosaur Land, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.