Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Pat Long

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Your Portland Holiday

Our Portland holiday packages allow you to customise 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 Centre and KFC Yum Centre. Don't put off visiting this city any longer. The ultimate Portland holiday is a few clicks away with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • Dining
    Aug 9 - Aug 17

    Cottonwood Airport & Expo Hotel Louisville + Flight

    Shively
    8 nights
    3.5 star property
    8.6/10 - Excellent (1,003 reviews)
    "Breakfast was fresh and ready staff was super friendly and helpful checking in process was quick easy and she was very friendly "
    Reviewed May 19, 2026
    Return • London (LGW) - Louisville (SDF)
    LGW - SDF • 2 stops SDF - LGW • 2 stops
    £1,469
    £1,233
    per traveller
    found 1 day ago
    Cottonwood Airport & Expo Hotel Louisville
  • Property amenity
    Aug 9 - Aug 17

    Crowne Plaza Louisville Airport Expo Ctr by IHG + Flight

    Fairgrounds
    8 nights
    3.5 star property
    8.8/10 - Excellent (1,435 reviews)
    "This hotel is wonderful. It was completely remodel in 2024 they said. Rooms were spscish and nice. All staff from shuttle, to front desk, to the eaters were very friendly. We stayed one night got there late bc of our flight but they still picked us up at airport to get us to the hotel and the guy at from desk was super nice. We ate breakfast which you pay for but was nice and lots of food choices. We wonder the property and seen the outside patio with fire pit; would have been awesome in the..."
    Reviewed May 19, 2026
    Return • London (LGW) - Louisville (SDF)
    LGW - SDF • 2 stops SDF - LGW • 2 stops
    £1,487
    £1,237
    per traveller
    found 1 day ago
    Crowne Plaza Louisville Airport Expo Ctr by IHG
  • 4 restaurants, breakfast, lunch, dinner served; American cuisine
    Aug 9 - Aug 17

    Galt House Hotel Trademark Collection by Wyndham + Flight

    Downtown Louisville
    8 nights
    4.0 star property
    9.0/10 - Wonderful (4,170 reviews)
    "The room was very clean. The breakfast variety is OK."
    Reviewed May 20, 2026
    Return • London (LGW) - Louisville (SDF)
    LGW - SDF • 2 stops SDF - LGW • 2 stops
    £1,621
    £1,360
    per traveller
    found 1 day ago
    Galt House Hotel Trademark Collection by Wyndham
  • Reception
    Aug 9 - Aug 17

    Embassy Suites Louisville Downtown + Flight

    Downtown Louisville
    8 nights
    4.0 star property
    9.0/10 - Wonderful (1,248 reviews)
    "Room clean , staff outstanding. Enjoyed my stay . "
    Reviewed May 20, 2026
    Return • London (LGW) - Louisville (SDF)
    LGW - SDF • 2 stops SDF - LGW • 2 stops
    £1,539
    £1,304
    per traveller
    found 1 day ago
    Embassy Suites Louisville Downtown
  • Lobby lounge
    Aug 9 - Aug 17

    AC Hotel Louisville Downtown + Flight

    Downtown Louisville
    8 nights
    3.5 star property
    9.2/10 - Wonderful (656 reviews)
    "Great staff"
    Reviewed May 20, 2026
    Return • London (LGW) - Louisville (SDF)
    LGW - SDF • 2 stops SDF - LGW • 2 stops
    £1,516
    £1,303
    per traveller
    found 1 day ago
    AC Hotel Louisville Downtown

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
4.5/5(8 area reviews)

The cultural heart of the city beats with baseball, boxing and music, with sporting fields, live bands and a center for Muhammad Ali, the city’s most famous son.

Find hotels in Downtown Louisville

Top hotels in Portland

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
The price is £77 per night from 1 Jun to 2 Jun
£77
1 Jun - 2 Jun
includes taxes & fees
8.8/10 Excellent! (1,435 reviews)
"This hotel is wonderful. It was completely remodel in 2024 they said. Rooms were spscish and nice. All staff from shuttle, to front desk, to the eaters were very friendly. We stayed one night got there late bc of our flight but they still picked us up at airport to get us to the hotel and the guy ..."

Reviewed on 19 May 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 £136 per night from 21 May to 22 May
£136
21 May - 22 May
includes taxes & fees
9/10 Wonderful! (4,170 reviews)
"The room was very clean. The breakfast variety is OK."

Reviewed on 20 May 2026

Galt House Hotel Trademark Collection by Wyndham
Radisson Hotel Louisville North

Radisson Hotel Louisville North

3 out of 5
505 Marriott Drive Clarksville IN
Fully refundableReserve now, pay when you stay
The price is £48 per night from 11 Jun to 12 Jun
£48
11 Jun - 12 Jun
includes taxes & fees
7/10 Good! (3,072 reviews)
"Very outdated, the different floors smelled like smoke and mold. Bathrooms look like hospital bathrooms. Some rooms A/C worked, some didn't. Seems like its a trucker hotel, area is a little ratchet. There is a bar that is open to the public and safety wise idk how that works. Its an okay hotel but ..."

Reviewed on 19 May 2026

Radisson Hotel Louisville North
See all 2,125 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Portland travel package cost?
Starting from only , a travel package is your passport to cheap travel. Create your own Portland escape by picking from our wide range of flights, hotels and rental cars.
If I'm not able to travel, can I cancel my Portland travel package?
It is possible to cancel your Portland booking if your plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Portland?
Creating your own Portland holiday package with Expedia is an easy way to save. We offer access to over 550 air carriers and 1,000,000 hotel options around the globe. With such an amazing range to pick from, you'll have no worries putting together your dream trip.
Does Expedia offer Book Now, Pay Later Portland holidays?
Expedia has teamed up with online lender Klarna to make your next trip a little easier on the wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that works with your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: If you want to pay off your escape across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Portland?
Make sightseeing easier by staying in a hotel just a stone's throw away from Portland's biggest attractions. Churchill Downs and Muhammad Ali Centre are two traveller favourites.
What are the top hotels in Portland?
Book a room at The Brown Hotel. It's one of this neighbourhood's most popular hotels. Another well-known option in Portland is Hyatt Regency Louisville.
How far in advance should I book my Portland holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you can't book early, don't stress. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia Portland travel package include?
Flights, hotels and rental cars — we've got them all. With Expedia, you can create your Portland travel package your way. All you have to do is figure out just what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Portland travel package?
When you book your hotels, flights and car rentals together, you'll score awesome discounts. Whether you're planning an outdoor getaway in a chalet or would rather stay in an upscale city hotel, Expedia can make it happen for less.
Can I choose my airline with a Portland Expedia travel package?
With a travel package, you're always in charge. Whether you'd prefer to fly to Portland in coach or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.

Things to do

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

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

£95
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

£15
per adult
92% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Lace, Lunacy, and Loss: Louisville Ghost Tours

Lace, Lunacy, and Loss: Louisville Ghost Tours

£19
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
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. Flight-inclusive packages are ATOL protected.