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.
Sleep Inn & Suites Middletown - Goshen
Price was CA $1,098, price is now CA $874 per person
CA $874
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
8.6/10 Excellent! (1,002 reviews)
Easy check in, clean and smoke free, friendly staff, nice rooms, hot breakfast; would stay again!!!!
Reviewed on Jan 20, 2026
Microtel Inn & Suites by Wyndham Middletown
Price was CA $1,028, price is now CA $940 per person
CA $940
per person
Mar 25 - Mar 31
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Newburgh (SWF)
7/10 Good! (1,000 reviews)
The room was very clean. The staff was welcoming and polite. Not sure about The amenities was only there on a business trip. Overall would definitely stay again.
Reviewed on Dec 6, 2025
Howard Johnson by Wyndham Newburgh/West Point
Price was CA $692, price is now CA $633 per person
CA $633
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
6/10 (1,002 reviews)
The rooms are clean and well maintained with a fridge and microwave located inside the room. The staff were accommodating and welcoming.
Reviewed on Jan 24, 2026
Middletown Hotel Deals
Sleep Inn & Suites Middletown - Goshen
3491 Route 6 Middletown NY
Fully refundable
The price is CA $128 per night from Mar 2 to Mar 3
CA $128
CA $151 total
Mar 2 - Mar 3
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Yes
Reviewed on Jan 20, 2026
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 $141 per night from Feb 16 to Feb 17
CA $141
CA $167 total
Feb 16 - Feb 17
includes taxes & fees
9.2/10 Wonderful! (967 reviews)
We stayed during the recent snow service was great
Reviewed on Jan 27, 2026
Hampton Inn by Hilton Middletown
20 Crystal Run Crossing Middletown NY
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Feb 26 to Feb 27
CA $111
CA $131 total
Feb 26 - Feb 27
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Staff was friendly and efficient. Bed comfy, super quiet & safe. I stayed only to sleep for a few hours during a snowstorm to be close to the hospital down the road so I didn’t have to drive far in the snow. It was expensive but worth the safe commute to work. Their parking lot was plowed and ...
Reviewed on Jan 27, 2026
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.
