Middletown Holidays
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Top hotels in Middletown
Wayside Inn
Nostalgia and history are prime attractions of this lovely inn. The barkeep Justin was friendly and helpful
Reviewed on 16 Mar, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service.
Reviewed on 23 Mar, 2026
La Quinta Inn & Suites by Wyndham Winchester
Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming.
Reviewed on 23 Mar, 2026
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.
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* 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.
