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 2.542.261 ₫ per night from 8 Mar to 9 Mar
2.542.261 ₫
2.765.980 ₫ total
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (2,263 reviews)
The room was very large and spotless. Clean and filled with plenty towels!
Reviewed on 10 Feb 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is 1.817.620 ₫ per night from 11 Feb to 12 Feb
1.817.620 ₫
1.977.571 ₫ total
11 Feb - 12 Feb
includes taxes & fees
8.4/10 Very Good! (1,081 reviews)
Room was good for the price, staff was friendly and helpful
Reviewed on 4 Feb 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 3.282.135 ₫ per night from 8 Mar to 9 Mar
3.282.135 ₫
3.718.659 ₫ total
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Clean nice room Great location for restaurants
Reviewed on 28 Jan 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.
