Middletown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Stephanie Sutton
Top hotels in Middletown
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 2.846.837 ₫ per night from 4 Mar to 5 Mar
2.846.837 ₫
3.097.358 ₫ total
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (2,279 reviews)
Clean room. Comfortable bed. Easy in and out. Reasonably close to Old Town Winchester in historic district. Friendly staff.
Reviewed on 1 Mar 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is 3.183.766 ₫ per night from 9 Mar to 10 Mar
3.183.766 ₫
3.607.207 ₫ total
9 Mar - 10 Mar
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area
Reviewed on 2 Mar 2026
Sleep Inn & Suites Winchester near University
140 Costello Dr Winchester VA
Fully refundable
The price is 2.082.034 ₫ per night from 23 Mar to 24 Mar
2.082.034 ₫
2.265.252 ₫ total
23 Mar - 24 Mar
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Hotel needs updating and repair. Had hole in bathroom door and securiity latch was broken.
Reviewed on 23 Feb 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.
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 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.
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.
