Portland Holidays
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- Rest easyPackages with flights are ATOL protected
Your Portland Holiday
Our Portland holiday packages allow you to customise your own adventure. Tailor your journey to your style and interests and make the most of your time in this fabulous city. If your trip to Portland includes a little sightseeing, take in well-known attractions like Churchill Downs, Muhammad Ali Centre and KFC Yum Centre. Don't put off visiting this city any longer. The ultimate Portland holiday is a few clicks away with Expedia.
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.
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.
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.
Old Louisville
Old Louisville is known for its ample dining options, and you can make a stop by Ohio River Valley and Conrad-Caldwell House Museum while in the area.
Top hotels in Portland
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
£138
9 Sept - 10 Sept
includes taxes & fees
9/10 Wonderful! (4,271 reviews)
"Always a pleasure everytime I'm in Louisville, this is where i stay."
Reviewed on 8 Sept 2026
Holiday Inn Express & Suites Louisville Downtown by IHG
800 W Market St Louisville KY
£99
13 Sept - 14 Sept
includes taxes & fees
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
£173
9 Sept - 10 Sept
includes taxes & 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.
Frequently asked questions
How much does a Portland travel package cost?
Starting from only , a travel package is your passport to cheap travel. Create your own Portland escape by picking from our wide range of flights, hotels and rental cars.
If I'm not able to travel, can I cancel my Portland travel package?
It is possible to cancel your Portland booking if your plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Portland?
Creating your own Portland holiday package with Expedia is an easy way to save. We offer access to over 550 air carriers and 1,000,000 hotel options around the globe. With such an amazing range to pick from, you'll have no worries putting together your dream trip.
Does Expedia offer Book Now, Pay Later Portland holidays?
Expedia has teamed up with online lender Klarna to make your next trip a little easier on the wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that works with your budget. Consider these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: If you want to pay off your escape across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: When you come across an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.
Where should I stay in Portland?
Make sightseeing easier by staying in a hotel just a stone's throw away from Portland's biggest attractions. Churchill Downs and Muhammad Ali Centre are two traveller favourites.
What are the top hotels in Portland?
Book a room at The Brown Hotel. It's one of this neighbourhood's most popular hotels. Another well-known option in Portland is Hyatt Regency Louisville.
How far in advance should I book my Portland holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you can't book early, don't stress. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia Portland travel package include?
Flights, hotels and rental cars — we've got them all. With Expedia, you can create your Portland travel package your way. All you have to do is figure out just what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Portland travel package?
When you book your hotels, flights and car rentals together, you'll score awesome discounts. Whether you're planning an outdoor getaway in a chalet or would rather stay in an upscale city hotel, Expedia can make it happen for less.
Can I choose my airline with a Portland Expedia travel package?
With a travel package, you're always in charge. Whether you'd prefer to fly to Portland in coach or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
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 lively bars while you're in the area.
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 acclaimed theatre scene and entertainment choices.
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.
Things to do
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
£15
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
£95
per adult
94% of travellers recommend
General Admission Ticket to Frazier History Museum
£12
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.