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 3.201.768 ₫ per night from 19 May to 20 May
3.201.768 ₫
3.794.805 ₫ total
19 May - 20 May
includes taxes & fees
9.2/10 Wonderful! (433 reviews)
"was nice and my gf enjoyed it"
Reviewed on 17 May 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.197.166 ₫ per night from 1 Jun to 2 Jun
2.197.166 ₫
2.489.390 ₫ total
1 Jun - 2 Jun
includes taxes & fees
9/10 Wonderful! (1,021 reviews)
"Room was super clean, staff friendly and knowledgeable. Breakfast was fresh but wish they had waffle maker."
Reviewed on 18 May 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.960.384 ₫ per night from 31 May to 1 Jun
2.960.384 ₫
3.220.897 ₫ total
31 May - 1 Jun
includes taxes & fees
9/10 Wonderful! (860 reviews)
"The room was spotless! Bed was so very comfortable. Breakfast was just right!"
Reviewed on 17 May 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 Battlefield Foundation
After visiting Cedar Creek Battlefield Foundation, make a plan to see the other sights and activities in Middletown. Amble around this vibrant area's riverfront or experience its entertainment venues.
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.
