Portland Vacations from $542
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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.
The Latest Portland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Stellar Suites
Downtown Louisville
Price was $654, price is now $542 per person
$542
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9.6/10 Exceptional! (142 reviews)
It is a very nice property - large room, kitchenette, new furnishings, and very clean. It's in a nice neighborhood with lots of clubs and restaurants nearby. Check-in is done online, there is no lobby, which makes it lass personal than other hotels. However, the good rates make for it.
Reviewed on Jul 27, 2026
Cottonwood Airport & Expo Hotel Louisville
Shively
Save 100% on your flight
Price was $1,788, price is now $1,342 per person
$1,342
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
The room was clean
Reviewed on Jul 28, 2026
Studio 6 Suites Louisville, KY – Airport/Expo Center
Highland Park
Price was $1,589, price is now $1,287 per person
$1,287
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
7.4/10 Good! (702 reviews)
The location seemed off but very quiet even tho it was a lot going on that weekend would stay again
Reviewed on Jul 28, 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.
Portland Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $170 total per night from Aug 17 to Aug 18
$170 total
Aug 17 - Aug 18
Total with taxes and fees
Omni Louisville Hotel
400 S. 2nd Street Louisville KY
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $187 total per night from Aug 2 to Aug 3
$187 total
Aug 2 - Aug 3
Total with taxes and fees
9.4/10 Exceptional! (2,031 reviews)
"I booked a king bed, upon arrival, they no longer had myvreserved room available"
Reviewed on Jul 29, 2026
Derby City Gaming & Hotel - A Churchill Downs Property
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $133 total per night from Aug 2 to Aug 3
$133 total
Aug 2 - Aug 3
Total with taxes and fees
9.4/10 Exceptional! (2,397 reviews)
"A1 perfect"
Reviewed on Jul 29, 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.
Stay near popular Portland attractions
Things to do
Kentucky Derby Museum - Admission with Guided Track Visit
$25
per adult
88% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
$25
per adult
92% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
$129
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.