Middletown Holidays

Photo by Samantha Keyes

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Top hotels in Middletown

Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is S$144 per night from 21 Sept to 22 Sept
S$144
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (395 reviews)
"What a lovely place. We spent a night here, and the facility was historic and beautiful. Our room was clean and comfortable. The staff could not have been kinder and more welcoming. We really enjoyed talking with them about the history of the area. I hope we can stay here again!!"

Reviewed on 24 Aug, 2025

Wayside Inn
Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2 out of 5
91 Reliance Road, Middletown, VA
Fully refundableReserve now, pay when you stay
The price is S$95 per night from 28 Sept to 29 Sept
S$95
28 Sept - 29 Sept
includes taxes & fees
5.6/10 (287 reviews)
"I loved staying here!"

Reviewed on 29 Aug, 2025

Econo Lodge Inn & Suites
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$151 per night from 23 Sept to 24 Sept
S$151
23 Sept - 24 Sept
includes taxes & fees
9.2/10 Wonderful! (2,152 reviews)
"Easy access to the highway as we passed through."

Reviewed on 13 Sept, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 613 properties in Middletown
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

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 and Belle Grove National Historical Park

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.