Middletown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Middletown Vacation

Reserve a Middletown vacation package that includes everything you need and nothing you don't. Good for nightlife, distilleries and craft breweries and shopping, consider staying in the neighborhood of East Market District. You'll want to take in some sights during your trip to Middletown. Make time for top attractions such as E.P. Tom Sawyer State Park, Mall St. Matthews and Springhurst Towne Center Shopping Center. Check out Expedia's extensive range of travel options and book your ideal vacation to Middletown now.

Top Holiday Package Deals in Middletown

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,165, price is now CA $922 per person
CA $922
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,171, price is now CA $940 per person
CA $940
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)
Website says handheld shower head, and it did not. It said smart tv, and there wasn't. Un top of that the cable kept pausing, saying bad connection. Previous leak in our room, 417.

Reviewed on Nov 2, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was CA $1,269, price is now CA $1,041 per person
CA $1,041
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,902 reviews)
Great place to stay recommend it to everyone!!

Reviewed on Nov 2, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was CA $1,107, price is now CA $925 per person
CA $925
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Excelente servicio

Reviewed on Oct 31, 2026

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was CA $1,115, price is now CA $932 per person
CA $932
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)

Where to stay in Middletown

Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
A city skyline with various buildings, including a prominent KFC and a green-roofed structure.

Downtown Louisville

3 out of top 10 points of interest in this area

Explore "Museum Row" in the West Main District, catch a game at Louisville Slugger Field, or stroll across the pedestrian-only Big Four Bridge. Enjoy diverse attractions, restaurants, and the Louie Link skywalk.

Find hotels in Downtown Louisville

Middletown Hotel Deals

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 CA $190 per night from Nov 15 to Nov 16
CA $190
CA $224 total
Nov 15 - Nov 16
includes taxes & fees
Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
The price is CA $146 per night from Nov 25 to Nov 26
CA $146
CA $172 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,442 reviews)
"Absolutely gorgeous place to stay within walking distance to anything and everything you would want to do. Fantastic food at the cafe. We will absolutley want to stay again! I really enjoyed the stay, but communication about charges to the room were non-existent. They do put an extra charge for the ..."

Reviewed on Nov 1, 2026

The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Nov 9 to Nov 10
CA $125
CA $147 total
Nov 9 - Nov 10
includes taxes & fees
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,244 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Middletown vacation package cost?
From as low as CA $922. 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.

Stay near popular Middletown attractions

Southeast Christian Church

After visiting Southeast Christian Church, make a plan to see the other sights and activities in Louisville. You can enjoy the restaurants while in the area.
See properties

Things to do

Live Professional Wrestling Admission Ticket Every Thursday

Live Professional Wrestling Admission Ticket Every Thursday

CA $17
per adult
100% of travellers recommend
Live Professional Wrestling Admission Ticket Every Thursday
Louisville: Mystery Paint & Sip Night at a Trendy Brewery

Louisville: Mystery Paint and Sip Night at a Trendy Venue

CA $83
per adult
Louisville: Mystery Paint and Sip Night at a Trendy Venue
Historic Walking Tour of Victorian Louisville with Food & Bourbon

Historic Walking Tour of Victorian Louisville with Food & Bourbon

CA $182
per adult
80% of travellers recommend
Historic Walking Tour of Victorian Louisville with Food & Bourbon
See all activities in Louisville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.