
Upperville Holidays
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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.
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

Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
The price is AU$285 per night from 22 Mar to 23 Mar
AU$285
22 Mar - 23 Mar
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Excellent rooms, spa, staff, everything. Very enjoyable stay. The only reason it is not 5 stars is because there isn't enough variety of food on the menus. Please offer more vegetarian options. But otherwise, wonderful stay!
Reviewed on 25 Feb 2026

Hilton Garden Inn Dulles North
22400 Flagstaff Plaza Ashburn VA
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 13 Mar to 14 Mar
AU$169
13 Mar - 14 Mar
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Staff was very friendly, always enjoy this property.
Reviewed on 23 Feb 2026

Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
The price is AU$1,026 per night from 5 Mar to 6 Mar
AU$1,026
5 Mar - 6 Mar
includes taxes & fees
9.2/10 Wonderful! (384 reviews)
For over a decade, staying at Salamander Middleburg was on my bucket list. As a young professional, I always heard raving reviews but felt priced out. So when a friend and I finally secured a Presidents Day weekend stay around $600 per night, we were excited for a true luxury experience. Unfortunately, ...
Reviewed on 22 Feb 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.
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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.












