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
Econo Lodge Inn & Suites Middletown - Winchester South
91 Reliance Road Middletown VA
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Jul 8 to Jul 9
CA $88
CA $97 total
Jul 8 - Jul 9
includes taxes & fees
5.8/10 (315 reviews)
"Check-in took almost 30 minutes. Dogs on property without leash, barking consistently in and outside of the facility. Staff went into my room while I was still checked in and left door wide open with my valuables inside. Absolutely unacceptable."
Reviewed on Jun 16, 2026
Wayside Inn
7783 Main St Middletown VA
The price is CA $172 per night from Jun 28 to Jun 29
CA $172
CA $204 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (438 reviews)
"A historical inn with charming features and friendly, helpful staff."
Reviewed on Jun 15, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Jul 23 to Jul 24
CA $123
CA $139 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,008 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
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.
Stay near popular Middletown attractions
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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.
