Upperville Holidays
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- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Your Upperville Holiday
When you choose a Upperville holiday package, you can relax and enjoy your getaway to the fullest. Uncover the sights and sounds of this fascinating city knowing that everything has been taken care of in advance. During your trip to Upperville, take all the time you need for sightseeing. A fantastic place to begin is Sky Meadows State Park. Expedia is here to help you escape the everyday. Tailor your holiday to Upperville to match your travel style, whatever that may be.
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 |
Top hotels in Upperville
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is £68 per night from 24 May to 25 May
£68
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Breakfast was minimal, but everything was excellent about the property! Staff, cleanliness and comfort were top notch!
Reviewed on 13 May 2026
Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
The price is £214 per night from 25 May to 26 May
£214
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Great stay
Reviewed on 12 May 2026
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
The price is £501 per night from 17 May to 18 May
£501
17 May - 18 May
includes taxes & fees
9.2/10 Wonderful! (393 reviews)
Spa was good, restaurants are good and food too, amenities are nice, air conditioning in the room was very loud all night long, woke me up several times, staff at the pool were not properly trained, we were asked to spell tequila and Chardonnay several times.
Reviewed on 25 Apr 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. Flight-inclusive packages are ATOL protected.
