
Middletown Vacation Packages
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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.
Top Middletown Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
per person
Oct 20 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.4/10 Very Good! (1,004 reviews)
The ad on Expedia said, "Breakfast included," except breakfast was a bag of trail mix and 2 granola bars. At 8:30 or 9am, I went to get just a little more coffee but it was all gone. Otherwise, everything was fine.
Reviewed on Jul. 28, 2025


Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen
3491 Route 6, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Aug 24 to Aug 25
CA $133
CA $158 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Rssb
"The staff was super friendly and the place was nice and clean. Comfortable bed and updated bathroom."
Reviewed on Jul. 30, 2025

Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 10 to Aug 11
CA $139
CA $165 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (937 reviews)
"Very clean and friendly staff the breakfast was good but a long wait since it was only 1 staff"
Reviewed on Jul. 29, 2025

La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E, Middletown, NY
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from Aug 3 to Aug 4
CA $160
CA $189 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (771 reviews)
"Place was great have stayed here many times."
Reviewed on Jul. 30, 2025
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
Orange County Fair Speedway
Catch an event at Orange County Fair Speedway during your trip to Mechanicstown. Discover the area's festivals and churches.
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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.