Middletown Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Aug 10 - Aug 14

    Days Inn by Wyndham Cave City + Flight

    Cave City
    3 nights
    2.0 star property
    7.2/10 - Good (1,007 reviews)
    ";"
    Reviewed June 1, 2026
    Roundtrip Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG1 stop CVG - NRT1 stop
    ¥304,635
    ¥299,763
    per traveler
    found 1 day ago
    Days Inn by Wyndham Cave City
  • Aug 11 - Aug 14

    Derby City Gaming & Hotel - A Churchill Downs Property + Flight

    Louisville
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,197 reviews)
    "Very nice for great price!"
    Reviewed June 10, 2026
    Roundtrip Tokyo (NRT) - Louisville (SDF)
    NRT - SDF1 stop SDF - HND1 stop
    ¥331,581
    ¥319,576
    per traveler
    found 1 day ago
    Derby City Gaming & Hotel - A Churchill Downs Property
  • Aug 10 - Aug 14

    Grand Victorian Inn + Flight

    Park City
    3 nights
    3.5 star property
    9.0/10 - Wonderful (733 reviews)
    "We enjoyed our stay at the Grand Victorian. The owners and staff were very friendly and helpful. Our room was clean and the bed was comfortable. There is some train noise but we didn’t hear it after 11 pm so it didn’t bother us or disturb our sleep. Breakfast was great. We would definitely recommend!"
    Reviewed June 9, 2026
    Roundtrip Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG1 stop CVG - NRT1 stop
    ¥331,868
    ¥325,767
    per traveler
    found 1 day ago
    Grand Victorian Inn
  • Aug 10 - Aug 14

    Homestay on Main by Twin Lakes Creamery + Flight

    Leitchfield
    3 nights
    3.0 star property
    8.8/10 - Excellent (45 reviews)
    "Very nice rooms with private bathroom"
    Reviewed May 23, 2026
    Roundtrip Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG1 stop CVG - NRT1 stop
    ¥316,025
    ¥310,997
    per traveler
    found 1 day ago
    Homestay on Main by Twin Lakes Creamery
  • Aug 10 - Aug 14

    Twin Lakes Creamery, Grill & Inn + Flight

    Leitchfield
    3 nights
    3.0 star property
    9.0/10 - Wonderful (138 reviews)
    "Beautiful setting Room was comfortable and spacious"
    Reviewed May 31, 2026
    Roundtrip Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG1 stop CVG - NRT1 stop
    ¥313,244
    ¥309,351
    per traveler
    found 1 day ago
    Twin Lakes Creamery, Grill & Inn

Where to stay in Middletown

Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown

Middletown Hotel Deals

Staybridge Suites - Louisville - East by IHG

Staybridge Suites - Louisville - East by IHG

3 out of 5
11711 Gateworth Way Louisville KY
Fully refundableReserve now, pay when you stay
The price is ¥13,710 per night from Jun 16 to Jun 17
¥13,710
¥16,130 total
Jun 16 - Jun 17
includes taxes & fees
8.2/10 Very Good! (721 reviews)
"I generally like the Staybridge hotel chain, but this property fell well short of my experiences with other Staybridge locations. The room was run-down and in serious need of renovation. Everything, from the carpet to the bed, looked worn and outdated. The front desk staff did mention that there ..."

Reviewed on Jun 9, 2026

Staybridge Suites - Louisville - East by IHG
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
The price is ¥14,116 per night from Jun 17 to Jun 18
¥14,116
¥16,609 total
Jun 17 - Jun 18
includes taxes & fees
8.8/10 Excellent! (1,531 reviews)
"One night stay next to airport, easy shuttle. Everything we needed to start our trip."

Reviewed on Jun 10, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG
Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
The price is ¥22,970 per night from Jun 27 to Jun 28
¥22,970
¥27,028 total
Jun 27 - Jun 28
includes taxes & fees
9/10 Wonderful! (4,184 reviews)
"Beautiful hotel. Clean and spacious rooms. Right in the middle of everything! Just walk! Easy drive to Churchill Downs."

Reviewed on Jun 8, 2026

Galt House Hotel Trademark Collection by Wyndham
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?
From as low as . Yes, you read that right. Our Middletown packages are a simple way to make your dollars go much further. Bundle your preferred flights, hotels and rental car and get to know this destination your way.
How do I get a cheap travel package to Middletown?
Our Middletown vacation packages promise plenty of savings for the savvy traveler. For the best deals, simply bundle your hotel, flights and extras (including activities) into a convenient package. But cheap prices are only the start of your next amazing adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotels globally to choose from. Whatever your budget or style, there's a package that's perfect for you.
Where should I stay in Middletown?
You'll want to stay where the action is. Many people like to book hotels around top attractions, such as Southeast Christian Church, Eastgate Shopping Center and Village Square Shopping Center.
What are the top hotels in Middletown?
Comfortable Suite Free Breakfast Buffet + Shared Outdoor Pool. Close To Ford Motor Company and Great Value 2 Bedroom Suite | Free Breakfast + Shared Outdoor Pool. Near Ford Motor Company are among the most popular hotels in Middletown. Why not take a look at the facilities and amenities at each and then decide?
How far in advance should I book my Middletown vacation?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Most international journeys on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't despair. Discounted prices appear from time to time within a few weeks of departure dates.
What does an Expedia Middletown travel package include?
Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to put together an amazing Middletown escape.
What should I know before booking a Middletown travel package?
We already have low prices. However, you'll pick up even more savings if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Middletown Expedia vacation package?
With a vacation package, you're in charge. Whether you're looking to fly to Middletown in economy or first class, simply select from the available airline options. Expedia has access to over 550 airline partners throughout the world.
If I'm not able to travel, can I cancel my Middletown vacation package?
Don't worry if you're rethinking your Middletown vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We know life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.