Middletown Vacations from $315
Book a Hotel + Flight or Car together to unlock savings
The Latest Middletown vacation packages
Price found within the past 48 hours. Click for updated prices.
Middletown Hotel Deals
Papa's Cabin - 40 acres & 5 acre lake!
Middletown MO
$197 nightly
$205 total
Oct 19 - Oct 20
Total with taxes and fees
10/10 Exceptional! (4 reviews)
"Clean, beautiful, serene and cozy! 10/10."
Reviewed on Sep 13, 2026
Bay Inn & Suites Troy
107 King Dr Troy MO
Fully refundableReserve now, pay when you stay
$65 nightly
$75 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (51 reviews)
"The room was clean and comfortable"
Reviewed on Oct 16, 2026
Holiday Inn Express Warrenton by IHG
1008 N Hwy 47 And Interstate 7 Warrenton MO
Fully refundable
$115 nightly
$131 total
Nov 15 - Nov 16
Total with taxes and fees
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.
Find the Best Middletown Vacation Packages
Middletown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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Frequently asked questions
How much does a Middletown vacation package cost?
You'll find cheap prices from $315 on Expedia for your Middletown escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Middletown costs.
What are the cheapest months to go to Middletown?
December, January and February are the best times to look for cheap Middletown vacation packages. Traveling in less busy periods means you can usually find lower prices on flights and hotels.
How many days is enough for Middletown?
The ideal length for your Middletown vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to go to all the leading sights and explore some hidden gems along the way.
How to find the best Middletown package deals?
Use Expedia's handy filters to help you find some fabulous Middletown package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Middletown package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Middletown vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Middletown?
If you're planning a spur-of-the-moment Middletown vacation, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Middletown break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.