Middletown Vacations

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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

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

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

Middletown MO
The price is AED 500 per night from Nov 21 to Nov 22
AED 500
AED 775 total
21 Nov - 22 Nov
includes taxes & fees
10/10 Exceptional! (4 reviews)
"Clean, beautiful, serene and cozy! 10/10."

Reviewed on 13 September 2026

Papa's Cabin - 40 acres & 5 acre lake!
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
The price is AED 263 per night from Dec 7 to Dec 8
AED 263
AED 301 total
7 Dec - 8 Dec
includes taxes & fees
9.4/10 Exceptional! (64 reviews)
"We were looking for a cheaper priced hotel as we were just stopping in for the night to sleep and getting on the road very early. Ironically, not realizing it, we had stayed at this hotel before. The hotel has done some really nice updates since our last visit, Hotel was clean, beds were comfortable ..."

Reviewed on 10 November 2026

Bay Inn & Suites Troy
Holiday Inn Express Warrenton by IHG

Holiday Inn Express Warrenton by IHG

2.5 out of 5
1008 N Hwy 47 And Interstate 7 Warrenton MO
Fully refundable
The price is AED 422 per night from Dec 13 to Dec 14
AED 422
AED 482 total
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (581 reviews)
"Parking good. Breakfast good. Clean"

Reviewed on 10 November 2026

Holiday Inn Express Warrenton by IHG
See all 57 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.

Frequently asked questions

How much does a Middletown vacation package cost?
Offering great value package deals 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 travelers wishing to save money.
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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: Once you've settled on your dates and duration, lock in the right Middletown vacation package for you.