Upperville Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Upperville Holiday
Cuisine, art, entertainment and more … It's all waiting for you with an Upperville holiday package. And with the ability to customise your city break, it's guaranteed to be one to remember. Sky Meadows State Park is among the big-ticket attractions to add to your itinerary during a trip to Upperville. Expedia will help you escape your daily routine. Tailor your holiday to Upperville to match your travel style, whatever that may look like.
Upperville Holiday
Upperville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Washington Dulles Intl. Airport (IAD) |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Barrel Oak Winery, The Boxwood Winery and Philip Carter Winery |
Our pick of the best Upperville Hotel Deals
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 29 June to 30 June
AU$142
29 June - 30 June
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Staff was very nice"
Reviewed on 2 June 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 21 June to 22 June
AU$173
21 June - 22 June
includes taxes & fees
9/10 Wonderful! (902 reviews)
"Amazing hotel, allowed me to check in early. Very nice and clean rooms"
Reviewed on 3 June 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$108 per night from 7 June to 8 June
AU$108
7 June - 8 June
includes taxes & fees
8.6/10 Excellent! (1,052 reviews)
"The room was very clean and the staff was friendly."
Reviewed on 2 June 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
