Middletown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Stephanie Sutton
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Middletown Holiday
Our pick of the best 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 NZ$120 per night from 1 July to 2 July
NZ$120
1 July - 2 July
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 16 June 2026
Wayside Inn
7783 Main St Middletown VA
The price is NZ$255 per night from 28 June to 29 June
NZ$255
28 June - 29 June
includes taxes & fees
9.2/10 Wonderful! (438 reviews)
"A historical inn with charming features and friendly, helpful staff."
Reviewed on 15 June 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 6 July to 7 July
NZ$200
6 July - 7 July
includes taxes & fees
9/10 Wonderful! (1,005 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 June 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.
Discover the most popular places to visit in Middletown
Belle Grove Plantation
Find out about the history of Middletown when you spend time at Belle Grove Plantation. Wander the riverfront or discover the mountain views in this vibrant area.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
