Portland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Pat Long

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 10 - Aug 14

    Days Inn by Wyndham Cave City + Flight

    Cave City
    3 nights
    2.0 star property
    7.2/10 - Good (1,007 reviews)
    ";"
    Reviewed June 1, 2026
    Roundtrip • Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG • 1 stop CVG - NRT • 1 stop
    ￥304,635
    ￥299,763
    per traveler
    found 1 day ago
    Days Inn by Wyndham Cave City
  • 3 bars/lounges
    Aug 11 - Aug 14

    Derby City Gaming & Hotel - A Churchill Downs Property + Flight

    Louisville
    3 nights
    4.0 star property
    9.4/10 - Exceptional (2,195 reviews)
    "Awesome hotel for fans of horse racing. Really beautiful decor throughout. Great service too. We loved our stay!"
    Reviewed June 9, 2026
    Roundtrip • Tokyo (NRT) - Louisville (SDF)
    NRT - SDF • 1 stop SDF - HND • 1 stop
    ￥331,581
    ￥319,576
    per traveler
    found 1 day ago
    Derby City Gaming & Hotel - A Churchill Downs Property
  • Exterior
    Aug 10 - Aug 14

    Grand Victorian Inn + Flight

    Park City
    3 nights
    3.5 star property
    9.0/10 - Wonderful (732 reviews)
    "Diana was very welcoming and prepared a very nice breakfast each morning. Loved the train even at 2:00 am!"
    Reviewed May 29, 2026
    Roundtrip • Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG • 1 stop CVG - NRT • 1 stop
    ￥331,868
    ￥325,767
    per traveler
    found 1 day ago
    Grand Victorian Inn
  • Romantic Room, 1 King Bed, Non Smoking, Jetted Tub | Bathroom | Towels, soap, shampoo, toilet paper
    Aug 10 - Aug 14

    Homestay on Main by Twin Lakes Creamery + Flight

    Leitchfield
    3 nights
    3.0 star property
    8.8/10 - Excellent (45 reviews)
    "Very nice rooms with private bathroom"
    Reviewed May 23, 2026
    Roundtrip • Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG • 1 stop CVG - NRT • 1 stop
    ￥316,025
    ￥310,997
    per traveler
    found 1 day ago
    Homestay on Main by Twin Lakes Creamery
  • Business Room, 1 Queen Bed, Non Smoking | Memory foam beds, individually decorated, individually furnished, desk
    Aug 10 - Aug 14

    Twin Lakes Creamery, Grill & Inn + Flight

    Leitchfield
    3 nights
    3.0 star property
    9.0/10 - Wonderful (138 reviews)
    "Beautiful setting Room was comfortable and spacious"
    Reviewed May 31, 2026
    Roundtrip • Tokyo (NRT) - Cincinnati (CVG)
    NRT - CVG • 1 stop CVG - NRT • 1 stop
    ￥313,244
    ￥309,351
    per traveler
    found 1 day ago
    Twin Lakes Creamery, Grill & Inn

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
Landscape of Louisville

Downtown Louisville

3 out of top 10 points of interest in this area
4/5(1,844 area reviews)

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

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
The price is ￥14,094 per night from Jun 16 to Jun 17
￥14,094
￥16,583 total
Jun 16 - Jun 17
includes taxes & fees
8.8/10 Excellent! (1,528 reviews)
"Great affordable place to stay"

Reviewed on Jun 9, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG
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 ￥23,832 per night from Jun 27 to Jun 28
￥23,832
￥28,041 total
Jun 27 - Jun 28
includes taxes & fees
9/10 Wonderful! (4,184 reviews)
"Beautiful hotel. Clean and spacious rooms. Right in the middle of everything! Just walk! Easy drive to Churchill Downs."

Reviewed on Jun 8, 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 ￥25,497 per night from Jun 28 to Jun 29
￥25,497
￥29,999 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,922 reviews)
"For one of the best It lacks alot. The customer service agents at the font did not know much about the city. Also there is no market place to pick up water or any where to shop if you forgot anything"

Reviewed on Jun 9, 2026

Omni Louisville Hotel
See all 2,088 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.

Frequently asked questions

How much does a Portland vacation package cost?
Get your credit card ready, because a trip to Portland starts from only . 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.

Things to do

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

￥3,923
per adult
92% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

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

￥20,240
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
General Admission Ticket to Frazier History Museum

General Admission Ticket to Frazier History Museum

￥2,510
per adult
General Admission Ticket to Frazier History Museum
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.