Middletown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Stephanie Sutton
Top hotels in Middletown
Wayside Inn
7783 Main St Middletown VA
The price is 3.200.067 ₫ per night from 20 Apr to 21 Apr
3.200.067 ₫
3.792.792 ₫ total
20 Apr - 21 Apr
includes taxes & fees
9.2/10 Wonderful! (426 reviews)
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful
Reviewed on 16 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 3.217.977 ₫ per night from 26 Apr to 27 Apr
3.217.977 ₫
3.645.969 ₫ total
26 Apr - 27 Apr
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.359.885 ₫ per night from 26 Apr to 27 Apr
2.359.885 ₫
2.567.556 ₫ total
26 Apr - 27 Apr
includes taxes & fees
9.2/10 Wonderful! (1,448 reviews)
Very clean property, room. Staff was very friendly. Breakfast wasn’t continental but a big breakfast, complete! Pancakes, eggs, sausage cereal, pastries, fruit! Well worth the price.
Reviewed on 16 Apr 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.
