Portland Vacations from $444
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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.
Holiday Inn Express Louisville Airport Expo Center by IHG
Hayfield Dundee
Price was $560, price is now $444 per person
$444
per person
Jan 13 - Jan 17
found 12 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Upon entering the property the desk clerk was courteous however I had 2 rooms and they were separated. When walking to the rooms I noticed footprints on the floor and those same footprints were there when I checked out. There appeared to be a permanent ring around the bathtub in one of the rooms and the other room had a bottle top on the floor in a corner. It appears the cleaning staff are not really thorough. I will not return to this location.
Reviewed on Nov 5, 2026
Pillow and Paddock B&B
Save 100% on your flight
Price was $1,032, price is now $697 per person
$697
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Crowne Plaza Louisville Airport Expo Ctr by IHG
Fairgrounds
Price was $713, price is now $524 per person
$524
per person
Jan 13 - Jan 17
found 12 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
8.8/10 Excellent! (1,902 reviews)
I’ve stayed here 5 times for work. Very convenient. The wait staff at the breakfast rush is extremely inconsistent with what is or isn’t included with the breakfast vouchers but that’s likely just due to turn over. Every morning we’ve had someone new.
Reviewed on Nov 5, 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
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.
Portland Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $160 total per night from Nov 15 to Nov 16
$160 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (4,452 reviews)
"Waited an entire day just to get our roo"
Reviewed on Nov 5, 2026
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Nov 25 to Nov 26
$153 total
Nov 25 - Nov 26
Total with taxes and fees
9.4/10 Exceptional! (1,457 reviews)
"ccc"
Reviewed on Nov 5, 2026
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Nov 15 to Nov 16
$107 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (2,613 reviews)
"I would make a suggestion that you have a mini fridge for leftover food from eating downstairs or complimentary waters maybe in room. Besides that the room and hotel is lovely!"
Reviewed on Nov 5, 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 - General Admission and Guided Track Visit
$24
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
$129
per adult
94% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
$29
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.