Name: TRU By Hilton Winchester
Price range: CA $108
Rating: 9

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Your Upperville Vacation

When you choose a Upperville vacation 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 vacation to Upperville to match your travel style, whatever that may be.

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Upperville Hotel Deals

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

CA $141

CA $159 total

Jul 6 - Jul 7

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

"Excellent hotel, very clean, nice beds."

Reviewed on Jun 15, 2026

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

Fully refundableReserve now, pay when you stay

CA $108

CA $119 total

Jul 5 - Jul 6

includes taxes & fees

9/10 Wonderful! (961 reviews)

"It would be nice to have a microwave and coffee/tea in the room"

Reviewed on Jun 17, 2026

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA

Fully refundableReserve now, pay when you stay

CA $272

CA $368 total

Jul 8 - Jul 9

includes taxes & fees

8.8/10 Excellent! (1,000 reviews)

"Rooms were clean, bar staff was great"

Reviewed on Jun 14, 2026

See all 740 properties in Upperville

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.