Middletown Holidays
Photo by Stephanie Sutton
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Top hotels in Middletown
Wayside Inn
7783 Main St Middletown VA
The price is €122 per night from 19 Apr to 20 Apr
€122
19 Apr - 20 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
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
The price is €87 per night from 26 Apr to 27 Apr
€87
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Very clean & functional room. Bed too soft and lLOUD thrumming noise all night long prevented sufficient sleep.
Reviewed on 13 Apr 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is €125 per night from 13 May to 14 May
€125
13 May - 14 May
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Great place in the middle of everything. Beautiful rooms.
Reviewed on 11 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.
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