Portland Vacation Packages

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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.
SpringHill Suites by Marriott Louisville Downtown

SpringHill Suites by Marriott Louisville Downtown

3 out of 5
Downtown Louisville
Price was CA $1,272, price is now CA $951 per person
CA $951
per person
Sep 11 - Sep 13
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Louisville (SDF)
8.4/10 Very good! (1,000 reviews)
Downtown but not in an area I want to walk around. Homelessness surrounding the hotel and some seedy businesses. Overall safer than some other cities but still not an area I was super comfortable with. It was good for a 1 night stay. Clean, decent breakfast with a nice view. Staff were very helpful.

Reviewed on Jul 27, 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $3,326, price is now CA $2,556 per person
CA $2,556
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
Fantastic customer service and the breakfast at the hotel was great!

Reviewed on Aug 1, 2026

Homewood Suites by Hilton Louisville Downtown, KY

Homewood Suites by Hilton Louisville Downtown, KY

3 out of 5
Downtown Louisville
Price was CA $1,465, price is now CA $1,277 per person
CA $1,277
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
9.4/10 Exceptional! (1,006 reviews)
Everyone was very helpful and the room was wonderful. We enjoyed the pool and breakfast as well. Would stay here again!

Reviewed on Aug 1, 2026

Hilton Garden Inn Louisville Downtown

Hilton Garden Inn Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was CA $1,269, price is now CA $1,151 per person
CA $1,151
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.4/10 Very good! (1,009 reviews)
Comfortable and clean

Reviewed on Aug 1, 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 $1,099, price is now CA $997 per person
CA $997
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
Staff was great

Reviewed on Jul 31, 2026

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

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.

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 $204 per night from Aug 15 to Aug 16
CA $204
CA $239 total
Aug 15 - Aug 16
includes taxes & fees
9/10 Wonderful! (4,208 reviews)
"Appreciated the size of the room as well as the hotel amenities (dining options and pool). The location was also ideal; close to everything I wanted to do downtown!"

Reviewed on Aug 1, 2026

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 CA $223 per night from Aug 9 to Aug 10
CA $223
CA $263 total
Aug 9 - Aug 10
includes taxes & fees
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
The price is CA $159 per night from Aug 2 to Aug 3
CA $159
CA $187 total
Aug 2 - Aug 3
includes taxes & fees
Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,076 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 $951. 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

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 lively festivals and acclaimed theater scene.
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 $183
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
92% 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.