
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.


Courtyard by Marriott Newburgh Stewart Airport
per person
Nov 1 - Nov 3
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newburgh (SWF)
8.2/10 Very Good! (671 reviews)
Staff was friendly and attentive to any needs I may have had, I definitely would stay here again
Reviewed on Aug. 6, 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 $140 per night from Sep 7 to Sep 8
CA $140
CA $166 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"Breakfast items not available after 9am."
Reviewed on Aug. 11, 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 $163 per night from Aug 25 to Aug 26
CA $163
CA $192 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (781 reviews)
"Bed comfort"
Reviewed on Aug. 9, 2025

Courtyard by Marriott Middletown Goshen
24 Crystal Run Xing, Middletown, NY
The price is CA $139 per night from Aug 17 to Aug 18
CA $139
CA $165 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (947 reviews)
"Very convenient. Nice front desk employee but needed to wait a while for multiple people checking in. Loved the lobby/bar but did not have time to take advantage. My only complaint is that the option for breakfast should be described to everyone checking in."
Reviewed on Aug. 9, 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.