Middletown Vacations from $326
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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.
The Latest Middletown Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Galt House Hotel Trademark Collection by Wyndham
Downtown Louisville
Price was $459, price is now $326 per person
$326
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (3,770 reviews)
It was very clean. I will be coming back
Reviewed on Dec 26, 2025
Hotel Distil, Autograph Collection
Downtown Louisville
Price was $978, price is now $708 per person
$708
per person
Mar 13 - Mar 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (422 reviews)
Great location. Great restraunt, great staff. Pleasurable experience!
Reviewed on Nov 30, 2025
Homewood Suites by Hilton Louisville Downtown, KY
Downtown Louisville
Price was $898, price is now $655 per person
$655
per person
Mar 13 - Mar 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.2/10 Wonderful! (1,004 reviews)
No, the breakfast menu was not fresh and there was some fruits that are old
Reviewed on Dec 25, 2025
The Grady
Downtown Louisville
Price was $938, price is now $689 per person
$689
per person
Mar 13 - Mar 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,001 reviews)
We had a pleasant stay at the Grady Hotel. The staff was extremely friendly and accommodating from start to finish. We were initially placed in a room near the elevator, but after mentioning the noise, they quickly moved us without any issue, which we really appreciated.
The room and bathroom were very clean overall. We did notice some stains on the bed sheets, which was a bit disappointing, but aside from that, everything was well maintained.
The on-site restaurant was a highlight of our stay—the ambiance was great, and it had a really nice vibe. The hotel’s location is also a big plus, with several museums and downtown attractions within easy walking distance, making it very convenient for exploring the area.
Overall, a solid experience with excellent service, and we’d consider staying again.
Reviewed on Dec 25, 2025
Hancock House
Downtown Louisville
Price was $657, price is now $509 per person
$509
per person
Mar 13 - Mar 17
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.2/10 Very Good! (245 reviews)
The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay.
Reviewed on Oct 31, 2025
Where to stay in Middletown
Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
Downtown Louisville
3 out of top 10 points of interest in this area
4/5(1,812 area reviews)
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.
Middletown Hotel Deals
Staybridge Suites - Louisville - East by IHG
11711 Gateworth Way Louisville KY
Fully refundable
$78 nightly
The price is $92 total per night from Jan 1 to Jan 2
$92 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8/10 Very Good! (674 reviews)
Yes breakfast was fresh
Reviewed on Dec 15, 2025
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $157 total per night from Jan 5 to Jan 6
$157 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,896 reviews)
Awesome place!
Reviewed on Dec 22, 2025
Crowne Plaza Louisville Airport Expo Ctr by IHG
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $114 total per night from Jan 25 to Jan 26
$114 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
8.8/10 Excellent! (1,062 reviews)
Nicely renovated, clean room
Reviewed on Dec 26, 2025
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.
Discover the most popular places to visit in Middletown
Kentucky Exposition Center
Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's acclaimed art scene and great live music.
Churchill Downs
Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.
Louisville Slugger Museum
Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.
Things to do
Kentucky Derby Museum - General Admission and Guided Track Visit
$20
per adult
90% of travellers recommend
Lace, Lunacy, and Loss: Louisville Ghost Tours
$32
per adult
Kentucky Derby Museum - Admission with Guided Track Visit
$22
per adult
100% of travellers recommend
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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.