Middletown Vacations

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Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Radisson Hotel Cincinnati Riverfront

Radisson Hotel Cincinnati Riverfront

668 W 5th St Covington KY
Fully refundable
NT$2,809
NT$3,156 total
Oct 18 - Oct 19
includes taxes & fees
Radisson Hotel Cincinnati Riverfront
Hilton Cincinnati Netherland Plaza

Hilton Cincinnati Netherland Plaza

35 W 5th St Cincinnati OH
Fully refundableReserve now, pay when you stay
NT$3,941
NT$4,701 total
Oct 18 - Oct 19
includes taxes & fees
8/10 Very Good! (1,865 reviews)
"One of the worst hotels I’ve ever stayed in. No AC, hot water takes forever, outdated and small rooms, uncomfortable mattresses, peeling paint and stains. The list goes on."

Reviewed on 2026/10/6

Hilton Cincinnati Netherland Plaza
Hyatt Regency Cincinnati

Hyatt Regency Cincinnati

151 West Fifth Street Cincinnati OH
Fully refundableReserve now, pay when you stay
NT$5,084
NT$6,065 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (1,652 reviews)
"Room was clean but the smell of mildew when we first entered our room"

Reviewed on 2026/10/6

Hyatt Regency Cincinnati
See all 2,951 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.

Stay near popular Middletown attractions

Start Skydiving

8.0/10 (2 reviews)
Experience the ultimate adrenaline rush at one of the world's largest dropzones, with breathtaking views of the Great Miami River. Experienced instructors ensure a premium skydiving adventure from training to landing.
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Land of Illusion

7.6/10 (8 reviews)
This seasonal adventure park transforms from summer water slides to fall haunted houses and winter light displays. Experience thrilling attractions for each season, from water courses to scream trails.
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Sorg Opera House

7.0/10 (2 reviews)
This 1891 theater showcases performances in a beautifully restored setting with ornate architectural details. Enjoy concerts and plays with excellent acoustics while surrounded by the venue's rich cultural history.
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Middletown Lyric Theatre

7.4/10 (3 reviews)
This intimate community theater showcased local talent through classic and contemporary productions since 1978. Visitors experienced quality performances in a cozy setting with post-show cast mingles on opening nights.
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Smith Park

7.2/10 (5 reviews)
Smith Park spans 7 acres across Middletown, featuring trails, sports fields, and a fishing pond. Enjoy a peaceful picnic or join community events hosted throughout the year.
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Seven Mile Winery

This family-owned boutique winery welcomes guests in a timber-framed barn overlooking a picturesque pond. Sample handcrafted fruit wines while enjoying live music and food trucks in this rustic Middletown retreat.
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Frequently asked questions

How much does a Middletown vacation package cost?
Offering excellent 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 save you more.
What are the cheapest months to go to Middletown?
You're likely to find reduced prices and better availability in November, December and January. Take a look at our cheap Middletown vacation packages and you could score some great off-season discounts.
How many days is enough for Middletown?
Generally, a handful of days is enough to explore the top attractions during your Middletown vacation. However, if you prefer to have more time to kick back or take day trips, consider extending your itinerary.
Is it worth booking a vacation package to Middletown?
Middletown has everything you need for an unforgettable escape. Get your Middletown vacation off to a flying start by exploring top attractions like Start Skydiving.
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, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure 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 usually best to lock in your vacation package well in advance.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a tailored Middletown vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Middletown?
If you're considering an impromptu Middletown getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Middletown?
  1. Pick your dates: The things you'd like to do in Middletown and your favorite season can help you decide when to go.
  2. Budget wisely: As well as the price of your hotel, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could arise during your trip to Middletown.
  3. Decide how long to go for: Now that you're up to speed on Middletown, you can work out the ideal length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Middletown vacation package that brings all your bookings together.

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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.