Name: TRU By Hilton Winchester
Price range: CA $145
Rating: 9

Photo by Stephanie Sutton

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Your Middletown Vacation

Let our vacation packages to Middletown inspire your next escape. You'll find a whole lot to like about this vibrant city, starting with the neighborhood of Shawnee Land, which is good for hiking and nature. Any trip to Middletown needs a well-thought-out itinerary. Fill yours with leading attractions like Jacksons Chase Golf Course, Blue Ridge Shadows Golf Club and Belle Grove Plantation. Don't put off exploring this destination any longer. Your ultimate Middletown vacation is a few clicks away with Expedia.

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Middletown Hotel Deals

Wayside Inn

7783 Main St Middletown VA

CA $167

CA $198 total

May 24 - May 25

includes taxes & fees

9.2/10 Wonderful! (433 reviews)

"was nice and my gf enjoyed it"

Reviewed on May 17, 2026

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

Fully refundableReserve now, pay when you stay

CA $113

CA $128 total

Jun 10 - Jun 11

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

"Staff were on top of everything, very roomy rooms, clean, and the hotel it self was clean. The morning meals was basic but plenty and fresh."

Reviewed on May 18, 2026

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

Fully refundableReserve now, pay when you stay

CA $145

CA $158 total

Jun 2 - Jun 3

includes taxes & fees

9/10 Wonderful! (868 reviews)

"A good quality, very well designed hotel, where everything is in the right place down to the smallest details like a night light in the bathroom. Comfortable bed and quiet room! Hotel is near new and in excellent condition!"

Reviewed on May 19, 2026

See all 619 properties in Middletown

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.