Upperville Holidays from AU$2,446

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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.

The Latest Upperville Holiday Deals

Price found within the past 48 hours. Click for updated prices.
SIXTY DC
Sofitel Washington DC Lafayette Square
Salamander Washington DC
Hotel Washington
Riggs Washington DC

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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 2 Nov to 3 Nov
AU$171
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (2,184 reviews)
"Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend."

Reviewed on 12 Oct 2025

La Quinta Inn & Suites by Wyndham Winchester
Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North

3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 2 Nov to 3 Nov
AU$150
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"This hotel was a little dated but very clean. The bathroom was very nice. I loved the shower area. But only issue was it water was leaking into the main floor thru the crack while I was taking shower."

Reviewed on 10 Oct 2025

Hilton Garden Inn Dulles North
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 2 Nov to 3 Nov
AU$198
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"Free Breakfast and parking. Close to many restaurants and shops"

Reviewed on 10 Oct 2025

Hampton Inn Winchester-University/Mall Area
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.