Middletown Holidays
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Middletown Holiday
Our pick of the best Middletown Hotel Deals
Wayside Inn
7783 Main St Middletown VA
The price is NZ$241 per night from 17 May to 18 May
NZ$241
17 May - 18 May
includes taxes & fees
9.2/10 Wonderful! (430 reviews)
Cozy and quaint. Felt like being in a home filled with lots of history! The people were very friendly in the restaurant and bar. Would definitely stay again.
Reviewed on 10 May 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$153 per night from 7 June to 8 June
NZ$153
7 June - 8 June
includes taxes & fees
9/10 Wonderful! (1,034 reviews)
Room was large with comfortable beds.
Reviewed on 10 May 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is NZ$248 per night from 25 May to 26 May
NZ$248
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
The hotel is in a great location in town, and in the region. My only negative comment is the charge to use the hotel parking lot. A little ridiculous in my opinion.
Reviewed on 10 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.
Discover the most popular places to visit in Middletown
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.
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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.
