Name: TRU By Hilton Winchester
Price range: CA $120
Rating: 9.2

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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

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA

Fully refundableReserve now, pay when you stay

CA $288

CA $387 total

Jul 7 - Jul 8

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

"The resort was gorgeous and well maintained. The proximity to various vineyards was perfect."

Reviewed on Jun 22, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

CA $123

CA $139 total

Jul 23 - Jul 24

includes taxes & fees

9/10 Wonderful! (1,009 reviews)

"Overall great experience - with that said their computer system wasnt working right. I was charged for the room twice (over and above the already charged payment from Expedia) and also a $100 security deposit. I brought it up the next day and it was immediately corrected. Nice hotel, good local, ..."

Reviewed on Jun 24, 2026

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

Fully refundableReserve now, pay when you stay

CA $120

CA $133 total

Jul 5 - Jul 6

includes taxes & fees

9.2/10 Wonderful! (988 reviews)

"Great overnight stay with the family. The rooms were clean and comfortable, and the kids absolutely loved the breakfast spread. I would recommend staying here if you're in the area or just passing through."

Reviewed on Jun 26, 2026

See all 751 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.