
Middletown Vacations from $232
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Your Middletown Vacation
Our Middletown vacation 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 vacation is just clicks away. Browse hotels, airfares and more on Expedia for a getaway that's tailored to suit your travel style.
The Latest Middletown vacation packages

The Crossroads Hotel, Newburgh
Reviewed on Jul 1, 2025

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Reviewed on Jul 3, 2025


La Quinta Inn & Suites by Wyndham Middletown-Goshen
Reviewed on Jul 11, 2025

Discover the most popular places to visit in Middletown
Orange County Fair Speedway
Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.
Orange County Fairgrounds
Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.
Galleria at Crystal Run
During your visit to Middletown, you can search for that perfect souvenir at Galleria at Crystal Run. While in this family-friendly area, you can savor the top-notch restaurants.
Middletown Hotel Deals

Reviewed on Jul 8, 2025

Reviewed on Jul 8, 2025

Reviewed on Jul 8, 2025
Find the Best Middletown Vacation Packages
Middletown Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 27,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Warwick Valley Winery and Distillery, Castle Fun Center and Paramount Theatre |
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- Paramount Theatre
- Orange County Fair Speedway
- Orange County Fairgrounds
- Galleria at Crystal Run
- Visit New Hampton
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- Visit Slate Hill
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- Orange County Genealogical Society
- Goshen Historic Track
- Harness Racing Museum and Hall of Fame
- Visit Goshen
- Visit Otisville
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