Middletown Holidays
Photo by Stephanie Sutton
Top hotels in Middletown
Econo Lodge Inn & Suites Middletown - Winchester South
91 Reliance Road Middletown VA
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 5 Jul to 6 Jul
S$110
5 Jul - 6 Jul
includes taxes & fees
5.8/10 (316 reviews)
"Room was clean. There was no pool I saw"
Reviewed on 27 Jun, 2026
Wayside Inn
7783 Main St Middletown VA
The price is S$186 per night from 29 Jun to 30 Jun
S$186
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (438 reviews)
"A historical inn with charming features and friendly, helpful staff."
Reviewed on 15 Jun, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 19 Jul to 20 Jul
S$124
19 Jul - 20 Jul
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 24 Jun, 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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