Portland Holidays from £642

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Red Roof Inn Charlestown

Red Roof Inn Charlestown

2 out of 5
per person
13 Sept - 17 Sept
found 10 hours ago
Return direct flight included
London (LON) to Louisville (SDF)
9/10 Wonderful! (12 reviews)
Clean, staff was nice.

Reviewed on 23 Jun 2025

Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
13 Sept - 17 Sept
found 10 hours ago
Return direct flight included
London (LON) to Louisville (SDF)
8.2/10 Very Good! (1,008 reviews)
Everything was great. Had a wonderful time.

Reviewed on 26 Jun 2025

Sun Outdoors Lake Rudolph

Sun Outdoors Lake Rudolph

2 out of 5
per person
13 Sept - 17 Sept
found 10 hours ago
Return direct flight included
London (LON) to Louisville (SDF)
10/10 Exceptional! (2 reviews)
It’s very relaxing and quiet in the middle of the woods and plenty to do there.

Reviewed on 25 Jun 2025

Aloft Louisville Downtown

Aloft Louisville Downtown

3 out of 5
Downtown Louisville
per person
1 Sept - 8 Sept
found 17 hours ago
Return direct flight included
London (LON) to Louisville (SDF)
9/10 Wonderful! (1,006 reviews)
The room was great as was the location. We were there 2 nights and housekeeping never came. There was a great selection of bourbon at the bar even if it was a bit expensive and the pours kind of small. Last, Saturday night in the lobby, they were blasting beat music all night that made it pretty hard to stay and have some drinks. Lots of people, including people that worked that, we complaining.

Reviewed on 27 Jun 2025

Best Western Plus French Lick

Best Western Plus French Lick

2.5 out of 5
per person
13 Sept - 17 Sept
found 10 hours ago
Return direct flight included
London (LON) to Louisville (SDF)
9.2/10 Wonderful! (1,000 reviews)
Everything was perfect except for the pillows. The pillows were to soft and very lumping.

Reviewed on 25 Jun 2025

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
Louisville showing street scenes and signage as well as a small group of people

Downtown Louisville

4 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

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 £114 per night from 2 Jul to 3 Jul
£114
2 Jul - 3 Jul
includes taxes & fees
8.8/10 Excellent! (3,388 reviews)
"Great place"

Reviewed on 25 Jun 2025

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 £159 per night from 4 Jul to 5 Jul
£159
4 Jul - 5 Jul
includes taxes & fees
9.2/10 Wonderful! (1,493 reviews)
"The hotel itself and the rooms are extremely beautiful and clean. However, outside is full of homeless people. Some are mentally ill and others are drug addicts and highly aggressive."

Reviewed on 24 Jun 2025

Omni Louisville Hotel
Radisson Hotel Louisville North
Radisson Hotel Louisville North
3 out of 5
505 Marriott Drive, Clarksville, IN
Fully refundable
The price is £49 per night from 29 Jul to 30 Jul
£49
29 Jul - 30 Jul
includes taxes & fees
6.8/10 (2,153 reviews)
"The outdoor pool is amazing. The indoor not so clean"

Reviewed on 27 Jun 2025

Radisson Hotel Louisville North
See all 1,952 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 £642, 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

Private Louisville Bourbon Tours

Private Louisville Bourbon Tours (Groups of 7-13) Old Fo & More

£125
per adult
Private Louisville Bourbon Tours (Groups of 7-13) Old Fo & More
Private Louisville Bourbon Tour

Private Louisville Bourbon Tour (Groups of 2-11) Old-Fo & More

£354
per adult
Private Louisville Bourbon Tour (Groups of 2-11) Old-Fo & More
Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

£24
per adult
Derby City Ghosts: Louisville Hauntings Tour
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.