Portland Holidays from £1,522

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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.
Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was £1,897, price is now £1,522 per person
£1,522
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Louisville (SDF)
9.2/10 Wonderful! (789 reviews)
Overall the room was nice and in a good location. However, the bed was terrible. My husband and I could not get more than a few hours of sleep due to how hard the mattress was

Reviewed on 14 Jul 2026

Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Save 100% on your flight
Price was £2,616, price is now £1,768 per person
£1,768
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Louisville (SDF)
8.6/10 Excellent! (1,006 reviews)

The Duke Hotel

The Duke Hotel

2 out of 5
Downtown Louisville
Price was £2,118, price is now £1,656 per person
£1,656
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Louisville (SDF)
8.6/10 Excellent! (19 reviews)
Found dead bugs; no other towels, bed sheets, or toiletries. No clean supplies available, and no one is coming to clean the place, especially since staying in the place for a long time.

Reviewed on 16 Jun 2026

Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

3 out of 5
Hayfield Dundee
Price was £1,869, price is now £1,523 per person
£1,523
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Louisville (SDF)
8.4/10 Very good! (1,246 reviews)
Nice affordable

Reviewed on 15 Jul 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was £2,091, price is now £1,720 per person
£1,720
per person
15 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LON) to Louisville (SDF)
9.6/10 Exceptional! (476 reviews)
The staff was their best asset! Very helpful, friendly, tried to accommodate any need!! Rooms were clean and beds were comfy!! We ate at the steakhouse in the hotel. Great food and our waitress was absolutely the best!!! The lobby could accommodate several groups of people!! Would stay there again!!

Reviewed on 13 Jul 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

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
Fully refundable
The price is £84 per night from 31 Jul to 1 Aug
£84
31 Jul - 1 Aug
includes taxes & fees
8.8/10 Excellent! (1,718 reviews)
"Stayed here twice. Excellent!!!! 10/10"

Reviewed on 15 Jul 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 £140 per night from 14 Aug to 15 Aug
£140
14 Aug - 15 Aug
includes taxes & fees
9/10 Wonderful! (4,174 reviews)
"If you are looking for comfortable but elevated experience, the Galt House is it. The rooms were spacious and overall amenities were accommodating and restaurants so delicious! My daughter and I had a wonderful time and will book again!"

Reviewed on 15 Jul 2026

Galt House Hotel Trademark Collection by Wyndham
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street Louisville KY
The price is £140 per night from 2 Aug to 3 Aug
£140
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (1,990 reviews)
"Customers service needs improvement. The young generations are more concerned about their identity!!"

Reviewed on 15 Jul 2026

Omni Louisville Hotel
See all 2,037 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
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Portland travel package cost?
Starting from only £1,522, 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.

Stay near popular Portland attractions

Kentucky Peerless Distilling Co.

You can take time to visit Kentucky Peerless Distilling Co. during your travels to Louisville. Attend a sporting event or simply enjoy the lively bars while you're in the area.
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

£97
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
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

£21
per adult
92% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
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.