
Middletown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Samantha Keyes
Top hotels in Middletown

Wayside Inn
7783 Main St, Middletown, VA
The price is 2.481.759 ₫ per night from 17 Aug to 18 Aug
2.481.759 ₫
2.999.737 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (392 reviews)
"We stayed last year on July 4th. ...really liked it...decided to make it an annual event. I like the small town atmosphere."
Reviewed on 7 Jul 2025

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is 2.694.481 ₫ per night from 1 Sept to 2 Sept
2.694.481 ₫
2.931.627 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,120 reviews)
"Liam was GREAT!! In addition to the young person that checked us in! This was a wonderful experience."
Reviewed on 12 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is 2.337.318 ₫ per night from 17 Aug to 18 Aug
2.337.318 ₫
2.621.788 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Very nice staff, clean. Restaurant on premises with good bkfst"
Reviewed on 11 Aug 2025
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.
Popular places to visit

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.
Cedar Creek Battlefield Foundation
You can learn about the history of Middletown with a visit to Cedar Creek Battlefield Foundation. Stroll along the riverfront or experience the entertainment venues in this vibrant area.
Cedar Creek and Belle Grove National Historical Park
Explore the great outdoors at Cedar Creek and Belle Grove National Historical Park, a lovely green space in Middletown. Stroll along the riverfront or experience the area's entertainment venues.