Portland Vacation Packages
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Your Portland Vacation
Our Portland vacation packages allow you to customize 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 Center and KFC Yum Center. Don't put off visiting this city any longer. The ultimate Portland vacation is a few clicks away with Expedia.
Top Holiday Package Deals in Portland
Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville
Shively
CA $1,135
per person
Nov 20 - Nov 24
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.6/10 Excellent! (1,004 reviews)
I had called the hotel in advance to tell them we were arriving late to check-in and was assured it would not be a problem. When we arrived there was no staff on property. We called and no one answered. We waited 2 1/2 hours and no staff returned. We ended up calling non-emergent police and they were not able to locate staff. Between 11:30-2am, there were people in and out of the lobby. There were stains on the carpet and the surrounding area did not seem very safe. We appreciated that the hotel did refund our room and hotels.com arranged another hotel for us.
Reviewed on Sep 16, 2026
Hyatt Regency Louisville
Downtown Louisville
CA $1,500
per person
Nov 20 - Nov 24
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (1,007 reviews)
Very clean, quiet and helpful staff. Close to convention centre and restaurants.
Reviewed on Sep 16, 2026
Louisville Marriott Downtown
Downtown Louisville
CA $1,408
per person
Nov 20 - Nov 24
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
The staff was amazing and the hotel was very nice and clean however, the biggest issues was the hotel was incredibly hot everywhere! The ladies restrooms were like saunas and it was difficult to maintain a decent temperature. The hotel really needs to address the temperature issues.
Reviewed on Sep 14, 2026
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
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.
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
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.
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.
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.
Portland Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
CA $226
CA $266 total
Oct 4 - Oct 5
includes taxes & fees
9/10 Wonderful! (4,273 reviews)
"Starbucks just wasn't staffed properly and I didn't know the hotel came with breakfast until the last morning of my stay"
Reviewed on Sep 16, 2026
Holiday Inn Express & Suites Louisville Downtown by IHG
800 W Market St Louisville KY
Fully refundableReserve now, pay when you stay
CA $164
CA $193 total
Sep 22 - Sep 23
includes taxes & fees
8.8/10 Excellent! (1,814 reviews)
"Hotel is ok. Breakfast very basic and always the same"
Reviewed on Sep 16, 2026
Crowne Plaza Louisville Airport Expo Ctr by IHG
830 Phillips Lane Louisville KY
CA $143
CA $169 total
Oct 15 - Oct 16
includes taxes & fees
8.8/10 Excellent! (1,846 reviews)
"Very convenient"
Reviewed on Sep 15, 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 vacation package cost?
Get your credit card ready, because a trip to Portland starts from only CA $1,135. When you combine your flights, hotels and more into a vacation 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 vacation 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 Center in Portland. Stay near these must-see attractions to make sightseeing a breeze.
How far in advance should I book my Portland vacation?
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 favorite 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 vacation goals are, you'll find a package to suit your budget.
Can I choose my airline with a Portland Expedia vacation package?
Yes — that's the beauty of an Expedia vacation 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 vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can cancel or change your Portland vacation 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 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 theater 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 browsing 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: 3-Hour Food and History Tour of NuLu District
CA $179
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
CA $28
per adult
94% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
CA $14
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.