Portland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Portland
Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
Downtown Louisville
4 out of top 10 points of interest in this area
The cultural heart of the city beats with baseball, boxing and music, with sporting fields, live bands and a center for Muhammad Ali, the city’s most famous son.
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.
St. Matthews
St. Matthews is noteworthy for its shopping, and you can make a stop at top attractions like Mall St. Matthews and Saint Matthews Pavilion Shopping Center.
Phoenix Hill
While Phoenix Hill isn't home to many top sights, Nulu Market Place and Louisville Slugger Field are some notable places to visit nearby.
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.
Top hotels in Portland
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
S$214
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (4,273 reviews)
"I loved the entire vibe if this hotel."
Reviewed on 21 Aug, 2026
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
S$238
23 Aug - 24 Aug
includes taxes & fees
9.4/10 Exceptional! (2,083 reviews)
"Such a excellent service,staff was so helpful!"
Reviewed on 20 Aug, 2026
Holiday Inn Express & Suites Louisville Downtown by IHG
800 W Market St Louisville KY
Fully refundableReserve now, pay when you stay
S$134
6 Sept - 7 Sept
includes taxes & fees
8.8/10 Excellent! (1,764 reviews)
"Quickly becoming my favorite stay in Louisville. Great location, great price, and great room."
Reviewed on 21 Aug, 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.
Frequently asked questions
How much does a Portland holiday package cost?
Get your credit card ready, because a trip to Portland starts from only . When you combine your flights, hotels and more into a holiday package, you'll score the best bargains.
How do I get a cheap travel package to Portland?
Browse and book everything in the one place with our Portland holiday packages. You'll find deals on hotels, flights, tours and more that'll keep your wallet happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 hotel options all over the world to select from, you have countless opportunities to mix and match your own way.
Where should I stay in Portland?
Visitors come from all corners of the globe to see Churchill Downs and Muhammad Ali Centre in Portland. Stay near these must-see attractions to make sightseeing a breeze.
How far in advance should I book my Portland holiday?
While not all airlines advertise ticket prices early, you can normally look up international flights on Expedia up to a year in advance. This is when you'll score some fantastic bargains. If you're booking last minute, you could still be in luck. Discounted prices occasionally emerge just weeks prior to departure.
What does an Expedia Portland travel package include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply choose your favourite bundle and get access to great discounts. Once you've made your booking, add on some tours and activities and watch your savings stack up. When it comes to creating your Portland break, you're the boss!
What should I know before booking a Portland travel package?
A travel package can be easier on the wallet than individually booking everything you need for your trip. For example, combine your hotels, flights and rental cars and save big. Whatever your holiday goals are, you'll find a package to suit your budget.
Can I choose my airline with a Portland Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Portland adventure.
If I'm not able to travel, can I cancel my Portland holiday package?
It's hard to predict what tomorrow might bring, so it's good to know that you can cancel or change your Portland holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
Stay near popular Portland attractions
Kentucky Peerless Distilling Co.
You can take time to visit Kentucky Peerless Distilling Co. during your travels to Louisville. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Lannan Park Trailhead
You can take time to visit Lannan Park Trailhead during your travels to Louisville.
Portland Museum
You can spend an afternoon studying the exhibits at Portland Museum during your travels in Louisville. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Boone Square Park
Boone Square Park is just one of the places to see in Louisville, so why not enjoy the other things to explore during your travels? Experience the area's great live music and entertainment choices.
Things to do
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
S$26
per adult
92% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
S$166
per adult
94% of travellers recommend
General Admission Ticket to Frazier History Museum
S$21
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.