Middletown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Middletown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hermann Grain Bins BNB
CA $2,191
per person
Nov 25 - Dec 1
found 22 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
6/10 (2 reviews)
It was so comfortable and uniquely and beautifully decorated! There was so many awesome areas to explore inside and outside of the Grain Bins. Food provided for breakfast was fresh and hot. There was perfectly cooked bacon, scrambled eggs and really moist corn muffins with homemade mango preservers! We were welcomed with fresh, homemade plum bread. Instructions for everything available to utilize and operate were easy to understand. I can’t wait to go back and I will tell all my friends and family about this unique and relaxing place.
Reviewed on May 22, 2026
Crowne Plaza St. Louis Airport by IHG
CA $1,437
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8/10 Very good! (1,001 reviews)
My bathroom wasn’t clean. Had a roach, hair pin and fake nail. Along the wall where sink is!
No blow dryer.
Front desk ladies were awesome!
Reviewed on Oct 15, 2026
Ready to book your vacation to Middletown?
Middletown Hotel Deals
Papa's Cabin - 40 acres & 5 acre lake!
Middletown MO
CA $165
CA $294 total
Oct 28 - Oct 29
includes taxes & 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
CA $94
CA $108 total
Oct 25 - Oct 26
includes taxes & fees
9.4/10 Exceptional! (50 reviews)
"Nice place to stay ."
Reviewed on Oct 16, 2026
Holiday Inn Express Warrenton by IHG
1008 N Hwy 47 And Interstate 7 Warrenton MO
Fully refundable
CA $163
CA $186 total
Nov 15 - Nov 16
includes taxes & 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.
Frequently asked questions
How much does a Middletown vacation package cost?
Offering great value package deals from CA $766 on Expedia, you'll be pleasantly surprised at how much a vacation to Middletown costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middletown?
If you're looking to book a cheap Middletown vacation package, consider planning a trip in January, February and June. You'll usually find lower prices on accommodations and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Middletown?
The ideal length for your Middletown vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to check out all the top attractions and discover some hidden treasures along the way.
How to find the best Middletown package deals?
Use Expedia's handy filters to find some unbeatable Middletown package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Middletown package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can customize your Middletown getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Middletown?
If you've got your Middletown travel dates confirmed, book early to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Middletown?
- Choose when to travel: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Middletown.
- Plan your budget wisely: Besides the cost of your hotel, you should consider other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Middletown.
- Work out your trip length: Consider how much time you want to spend exploring Middletown. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Combine your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Middletown vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
