Middletown Vacations from $243

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The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
 White House at Grand Central
Remodeled and Inviting Free EV
Hilton Garden Inn Chesterfield
The Cheshire
Ameristar Casino Resort and Spa
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Middletown Hotel Deals

Papa's Cabin - 40 acres & 5 acre lake!

Papa's Cabin - 40 acres & 5 acre lake!

Middletown MO
$197 nightly
The price is $205 total per night from Jul 23 to Jul 24
$205 total
Jul 23 - Jul 24
Total with taxes and fees
10/10 Exceptional! (2 reviews)
"We absolutely loved our stay at the cabin!! So much space to spread out inside, and the property & lake are so peaceful and enjoyable to explore. Though we only spent one night, we really loved it there, and will definitely be back when we are in the area visiting family!"

Reviewed on May 23, 2026

Papa's Cabin - 40 acres & 5 acre lake!
Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton

2.5 out of 5
425 E Veterans Memorial Pkwy Warrenton MO
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Aug 9 to Aug 10
$94 total
Aug 9 - Aug 10
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
"We got a double queen sized room, the bathroom was a little small and walk around space around the beds was also pretty small but the tv is nice sized and the beds were comfortable. The vending machine wouldn’t take $5 bills but the front desk gave me some change for various bills so we could use ..."

Reviewed on Jul 13, 2026

Baymont by Wyndham Warrenton
Bay Inn & Suites Troy

Bay Inn & Suites Troy

2.5 out of 5
107 King Dr Troy MO
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $88 total per night from Jul 23 to Jul 24
$88 total
Jul 23 - Jul 24
Total with taxes and fees
6.6/10 (266 reviews)
"The construction mentioned by others seems to be nearing completion and it looks really great! Still some things here and there, parking is pretty crowded but our room was very clean and bedding seemed new. Bed was comfy and we enjoyed our stay."

Reviewed on Jul 14, 2026

Bay Inn & Suites Troy
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 $243 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.