Middletown Vacation Packages
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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.
Middletown Hotel Deals
Wayside Inn
7783 Main St Middletown VA
The price is CA $167 per night from Jun 2 to Jun 3
CA $167
CA $198 total
Jun 2 - Jun 3
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
The price is CA $122 per night from Jun 3 to Jun 4
CA $122
CA $139 total
Jun 3 - Jun 4
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Very clean hotel,friendly staff"
Reviewed on May 21, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Jun 4 to Jun 5
CA $145
CA $158 total
Jun 4 - Jun 5
includes taxes & fees
9/10 Wonderful! (871 reviews)
"Room very clean .. great to play pool .. but at breakfast had to ask for more oatmeal as it was empty even though the woman was standing right there. She was not paying attention to what was needed"
Reviewed on May 20, 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.
