Middletown Packages (Flight + Hotel)

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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 ฿3,964 per night from 19 Apr to 20 Apr
฿3,964
฿4,698 total
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

Wayside Inn
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
The price is ฿2,871 per night from 12 Apr to 13 Apr
฿2,871
฿3,221 total
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
Breakfast was excellent and all the staff were very friendly.

Reviewed on 30 Mar 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 ฿3,582 per night from 6 Apr to 7 Apr
฿3,582
฿3,897 total
6 Apr - 7 Apr
includes taxes & fees
9.2/10 Wonderful! (2,270 reviews)
Clean room, it’s our second visit and still just as clean as last visit.

Reviewed on 3 Apr 2026

La Quinta Inn & Suites by Wyndham Winchester
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.