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.

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Middletown Hotel Deals

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Fully refundable
The price is CA $178 per night from Jul 26 to Jul 27
CA $178
CA $211 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (1,052 reviews)
"I will never ever stay at this sleeps inn the house keeping service is horrible and the staff hang out at night with their friends. Also a couple of people were outside smoking pot"

Reviewed on Jul 2, 2026

Sleep Inn & Suites Middletown - Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jul 26 to Jul 27
CA $175
CA $207 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Rooms were clean and A/C worked well. Lots of water pressure in the shower. Friendly staff."

Reviewed on Jul 2, 2026

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
20 Crystal Run Crossing Middletown NY
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jul 21 to Jul 22
CA $162
CA $191 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"All in all it feels like staying at a cheap motel but paying for a luxury apartment. It started with check in, we didn’t get a room until almost 5 when check in was at 3. We were offered no apologize or accommodations, just waited in the lobby for an hour. No one wanted to clean the building so rooms ..."

Reviewed on Jun 30, 2026

Hampton Inn by Hilton Middletown
See all 1,518 properties in Middletown
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.
All Inclusive Vacations
All Inclusive Vacations
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Stay near popular Middletown attractions

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)
Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.
See properties

Frequently asked questions

How much does a Middletown vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Middletown costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Middletown?
December, January and February are great times to look for cheap Middletown vacation packages. Travelling in less busy periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Middletown?
We'd recommend booking a Middletown vacation for a minimum of 2 days. This gives you enough time to tick off popular sights such as Galleria at Crystal Run and Harness Racing Museum and Hall of Fame, and also explore neighbourhoods like Scotchtown and Mechanicstown. You could even fit in a day trip from Middletown.
Is it worth booking a vacation package to Middletown?
It's easy to see why a Middletown vacation is on the must-do list of many travellers. Popular attractions like Orange County Fair Speedway are just the start of things to see and do here.
How to find the best Middletown package deals?
Finding a cheap Middletown package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Middletown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Middletown trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Middletown?
Land fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Middletown break.
How to plan a trip to Middletown?

  1. Choose your travel dates: What you plan to do in Middletown and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the price of your hotel, you should consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could arise during your trip to Middletown.
  3. Decide your trip length: Consider how much time you want to spend exploring Middletown. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your accommodations and airfare: After you've nailed down your dates and duration, lock in the ideal Middletown vacation package for you.

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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.