
Middletown Holidays from £631
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Your Middletown Holiday
Our Middletown holiday packages allow you to create your own adventure. Tailor your journey to your needs and interests and make the most of your time in this fabulous city. Orange County Fair Speedway, Galleria at Crystal Run and Orange County Fairgrounds are just a few of the many sights you'll want to see during your trip to Middletown. Your ultimate Middletown holiday is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
Top Middletown Flight + Hotel Deals

The Crossroads Hotel, Newburgh
Reviewed on 1 Jul 2025


Newburgh Inn
Reviewed on 24 Dec 2024

Holiday Inn Express & Suites Middletown - Goshen by IHG
Reviewed on 1 Jul 2025
Middletown Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 27,800 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Warwick Valley Winery and Distillery, Castle Fun Centre and Harness Racing Museum and Hall of Fame |
Top hotels in Middletown

Reviewed on 11 Jul 2025

Reviewed on 13 Jul 2025

Reviewed on 12 Jul 2025
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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. Flight-inclusive packages are ATOL protected.