Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,165, price is now CA $922 per person
CA $922
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Can’t wait to go back!

Reviewed on Nov 1, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,171, price is now CA $940 per person
CA $940
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)
Website says handheld shower head, and it did not. It said smart tv, and there wasn't. Un top of that the cable kept pausing, saying bad connection. Previous leak in our room, 417.

Reviewed on Nov 2, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was CA $1,269, price is now CA $1,041 per person
CA $1,041
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,902 reviews)
Property was great

Reviewed on Nov 2, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was CA $1,107, price is now CA $925 per person
CA $925
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Excelente servicio

Reviewed on Oct 31, 2026

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was CA $1,115, price is now CA $932 per person
CA $932
per person
Jan 6 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
A city skyline with various buildings, including a prominent KFC and a green-roofed structure.

Downtown Louisville

3 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.

Find hotels in Downtown Louisville

Portland Hotel Deals

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 CA $190 per night from Nov 15 to Nov 16
CA $190
CA $224 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (4,458 reviews)
"Second day had to go to front desk and proof I checked in because they listed me as a no show. Had a stranger enter my room because they rebooked it. Also had cleaning people enter the room. Finally got it straightened out. Now 8 days later they still haven’t released the $100 incedentals. Very few ..."

Reviewed on Nov 1, 2026

Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
The price is CA $146 per night from Nov 25 to Nov 26
CA $146
CA $172 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,442 reviews)
"Absolutely gorgeous place to stay within walking distance to anything and everything you would want to do. Fantastic food at the cafe. We will absolutley want to stay again! I really enjoyed the stay, but communication about charges to the room were non-existent. They do put an extra charge for the ..."

Reviewed on Nov 1, 2026

The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Nov 16 to Nov 17
CA $125
CA $147 total
Nov 16 - Nov 17
includes taxes & fees
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,091 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $922. 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

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.
See properties

Things to do

Louisville: 3-Hour Food and History Tour of NuLu District

Louisville: 3-Hour Food and History Tour of NuLu District

CA $182
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

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

CA $28
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $14
per adult
80% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking 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.