Portland Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, 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
Louisville showing street scenes and signage as well as a small group of people

Downtown Louisville

3 out of top 10 points of interest in this area
4.5/5(8 area reviews)

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.

Find hotels in Downtown Louisville

Top hotels in Portland

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 S$217 per night from 31 Oct to 1 Nov
S$217
31 Oct - 1 Nov
includes taxes & fees
8.8/10 Excellent! (3,644 reviews)
"Hated that the pool was closed for the season and there wasnt a microwave in the room, but room service was fast and amazing, the room was HUGE and super clean, everyone was so nice!! Already talking about booking again!!"

Reviewed on 24 Sept, 2025

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is S$302 per night from 19 Oct to 20 Oct
S$302
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (1,623 reviews)
"Upscale stay, beautiful property, and great location! We were able to walk to so many great restaurants and the hotel really made a great experience for our first time in Louisville. Will be returning!"

Reviewed on 21 Sept, 2025

Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,470 reviews)
"Great! Very clean as well and friendly"

Reviewed on 27 Sept, 2025

Get rates
Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,008 properties in Portland
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.

Things to do

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

S$26
per adult
90% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
The Samuel Culbertson Mansion sits at the heart of Millionaires Row.

Old Louisville Walking Tour Recommended by The New York Times! @ 4th and Ormsby

S$32
per adult
86% of travellers recommend
Old Louisville Walking Tour Recommended by The New York Times! @ 4th and Ormsby
Bourbon Bottle Hall selfie!

General Admission Ticket to Frazier History Museum

S$21
per adult
General Admission Ticket to Frazier History Museum
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. 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.