Portland Holidays

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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

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

Downtown Louisville is beloved for its fantastic nightlife. Take some time to explore sights in the area like Whiskey Row and KFC Yum Center.

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$199 per night from 2 Jul to 3 Jul
S$199
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (3,392 reviews)
"I had a great time . Everything was done with an excellent flare. Staff was very nice. Nothing wrong!"

Reviewed on 26 Jun, 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$278 per night from 3 Jul to 4 Jul
S$278
3 Jul - 4 Jul
includes taxes & fees
9/10 Wonderful! (1,496 reviews)
"The hotel itself and the rooms are extremely beautiful and clean. However, outside is full of homeless people. Some are mentally ill and others are drug addicts and highly aggressive."

Reviewed on 24 Jun, 2025

Omni Louisville Hotel
Radisson Hotel Louisville North
Radisson Hotel Louisville North
3 out of 5
505 Marriott Drive, Clarksville, IN
Fully refundable
The price is S$85 per night from 28 Jul to 29 Jul
S$85
28 Jul - 29 Jul
includes taxes & fees
6.8/10 (2,153 reviews)
"Whenever I’m"

Reviewed on 26 Jun, 2025

Radisson Hotel Louisville North
See all 1,952 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

Private Louisville Bourbon Tours

Private Louisville Bourbon Tours (Groups of 7-13) Old Fo & More

S$217
per adult
Private Louisville Bourbon Tours (Groups of 7-13) Old Fo & More
Private Louisville Bourbon Tour

Private Louisville Bourbon Tour (Groups of 2-11) Old-Fo & More

S$616
per adult
Private Louisville Bourbon Tour (Groups of 2-11) Old-Fo & More
Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

S$31
per adult
Derby City Ghosts: Louisville Hauntings Tour
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.