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 2.547.265 ₫ per night from 15 Feb to 16 Feb
2.547.265 ₫
2.771.425 ₫ total
15 Feb - 16 Feb
includes taxes & fees
9.2/10 Wonderful! (2,259 reviews)
Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience.
Reviewed on 31 Jan 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 10 Feb to 11 Feb
1.817.620 ₫
1.977.571 ₫ total
10 Feb - 11 Feb
includes taxes & fees
8.4/10 Very Good! (1,079 reviews)
Room was great and breakfast was ok but had waffles
Reviewed on 2 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 3.288.594 ₫ per night from 17 Feb to 18 Feb
3.288.594 ₫
3.725.977 ₫ total
17 Feb - 18 Feb
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.
