Middletown Vacations from $424
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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.
Hyatt Regency Louisville
Downtown Louisville
$604
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Room was nice and clean. At the same time, both the on site parking garage and the garage elevator were extremely dirty. Especially garage and elevator floors.
Reviewed on Oct 17, 2026
The Maple Retreat at Park Mammoth
$1,274
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Louisville (SDF)
9.2/10 Wonderful! (22 reviews)
Communication was proactive and showed a genuine concern for our comfort during our stay.
There was an error in double booking on the property’s end and they made extra accommodations for us and went out of their way to make sure we were taken care of.
The owner is a very kind person and reached out on a few occasions to ensure we had everything we needed.
The cabin was beautiful, well maintained, and clean, and had great amenities for cooking. We enjoyed the brand new grill outside and also used the fire pit and enjoyed the local hiking trail.
It is close to Mammoth Cave and we really enjoyed spending half the day at the park then relaxing at the cabin for the rest of the day.
Highly recommend!!!
(Side note - we are now at our next cabin destination of our road trip and we are missing the comfort and amenities at Maple Retreat!)
Reviewed on Aug 12, 2026
Regina's Country Livin'
$996
per person
Dec 22 - Dec 29
found 10 hours ago
Roundtrip flight included
Phoenix (PHX) to Louisville (SDF)
9.6/10 Exceptional! (14 reviews)
If I am ever doing something between Louisville and Lexington, I will be visiting Regina. This house was well-designed as a true BNB with excellent access/security, thoughtful decor, and an extremely welcoming atmosphere. The reviews praising the breakfast are true - but don't just go for the biscuits and gravy, go for the full experience.
Reviewed on Sep 28, 2026
Where to stay in Middletown
Find the best Middletown areas and neighborhoods for the activities you enjoy most. Learn more about Middletown
Downtown Louisville
4 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.
St. Matthews
Major shopping destination with the fifth-largest mall in Kentucky, Mall St. Matthews, and smaller centers along Shelbyville Road. Don't miss the historic St. Matthew's Episcopal Church and Holy Trinity.
Jeffersontown
Jeffersontown is known for its abundant dining options, and you can plan a trip to Jeffersontown Commons Shopping Center and Bluegrass Indoor Karting while you're in town.
Fairgrounds
1 out of top 10 points of interest in this area
While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.
Old Louisville
Boasting Victorian architecture and the highest concentration of stained glass windows in residential homes, Old Louisville offers a walkable neighborhood with pedestrian-only streets, diverse dining options, and attractions like Central Park and the Conrad-Caldwell House.
Middletown Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$140 nightly
$165 total
Nov 8 - Nov 9
Total with taxes and fees
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$156 nightly
$183 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (1,388 reviews)
"Nice hotel, very historic, but the bed was a full size, and the mattress was as hard as a rock."
Reviewed on Oct 16, 2026
Radisson Hotel Louisville North
505 Marriott Drive Clarksville IN
Fully refundable
$71 nightly
$81 total
Oct 25 - Oct 26
Total with taxes and fees
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
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.
Eastgate Shopping Center
During your visit to Louisville, you can find the perfect gifts to bring home at Eastgate Shopping Center. Discover the top-notch restaurants and lively festivals in this romantic area.
Renaissance Fun Park
Enjoy a fun-filled day at Renaissance Fun Park during your trip to Louisville. You can enjoy the restaurants while in the area.
Village Square Shopping Center
You can enjoy retail therapy at Village Square Shopping Center during your visit to Louisville. Discover the top-notch restaurants and acclaimed art scene in this romantic area.
Things to do
Live Professional Wrestling Admission Ticket Every Thursday
$12
per adult
100% of travellers recommend
Historic Walking Tour of Victorian Louisville with Food & Bourbon
$139
per adult
80% of travellers recommend
Private Louisville Food Tour with Food Tastings, Drinks & History
$350
per adult
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- Middletown Station Shopping Center
- Springhurst Towne Center Shopping Center
- Pewee Valley Vacations
- Avish Gardens Shopping Center
- Iceland Sports Complex
- Bluegrass Indoor Karting
- Hikes Point Plaza Shopping Center
- Louisville Mega Cavern
- Where to stay in Louisville
- Jeffersontown Commons Shopping Center
- Paddock Shops
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- Louisville Zoo
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- Eastgate Shopping Center
- Chamberlain Pointe Shopping Center
- Beckley Creek Park
- Southeast Christian Church
- Mall St. Matthews
- The Summit Shopping Center
- E.p. Tom Sawyer State Park
- Louisville Slugger Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.