Middletown Vacations from $610
Book a Hotel + Flight or Car together to unlock savings
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.
Pillow and Paddock B&B
$1,750
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 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
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.
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.
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.
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.
Middletown Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$136 nightly
$160 total
Nov 8 - Nov 9
Total with taxes and fees
9/10 Wonderful! (4,409 reviews)
"Not a good experience at all! Majorly overpriced! Will never stay here again!"
Reviewed on Oct 23, 2026
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$117 nightly
$137 total
Nov 23 - Nov 24
Total with taxes and fees
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$89 nightly
$105 total
Nov 9 - Nov 10
Total with taxes and fees
9.4/10 Exceptional! (2,584 reviews)
"Our stay was fantastic. We stayed in one of the large king suites and it was the size of a small house. The separate living area with another TV and large sectional was nice. Also for our room, they should note that the derby has practice from 5am until 10am. One of the windows faced the track and ..."
Reviewed on Oct 23, 2026
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
Louisville: Mystery Paint & Sip Night at a Trendy Brewery
$59
per adult
Historic Walking Tour of Victorian Louisville with Food & Bourbon
$139
per adult
80% of travellers recommend
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- Middletown Station Shopping Center
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- 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.