Portland Vacations from $395

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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.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $547, price is now $395 per person
$395
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
17.6/10 Exceptional! (962 reviews)
The shuttle service was by far the best ever! Derrick our regular driver definitely goes above & beyond for his riders. All the staff was always super friendly and helpful.

Reviewed on Nov 17, 2025

Hilton Garden Inn Louisville/Northeast

Hilton Garden Inn Louisville/Northeast

3 out of 5
Price was $786, price is now $573 per person
$573
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
18/10 Exceptional! (205 reviews)
Very clean. Good beds. Quiet. Supper available at the bar in the hotel.

Reviewed on Nov 17, 2025

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
Price was $670, price is now $499 per person
$499
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
18/10 Exceptional! (1,062 reviews)
Everything was amazing besides the juices taste water down and beverage machine wasn’t working for breakfast.

Reviewed on Nov 18, 2025

Courtyard by Marriott Louisville Airport

Courtyard by Marriott Louisville Airport

3 out of 5
Price was $576, price is now $452 per person
$452
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
18/10 Exceptional! (304 reviews)
Staff pleasant Room great

Reviewed on Nov 16, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $812, price is now $637 per person
$637
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
18/10 Exceptional! (1,003 reviews)
Room was great, but the service by the attendant that wait on me was exceptional in what she done for me.

Reviewed on Nov 8, 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 signage and street scenes as well as a small group of people

Downtown Louisville

4 out of top 10 points of interest in this area
4/5(1,812 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

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
$93 nightly
The price is $110 total per night from Nov 25 to Nov 26
$110 total
Nov 25 - Nov 26
Total with taxes and fees
8.8/10 Excellent! (3,777 reviews)
The hotel is beautiful and decorated for the holidays, the room was very nice, clean and comfortable. Had one amall issue with the air/heat unit being very loud, possibility in need of repair, otherwise we loved the room.

Reviewed on Nov 17, 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
$199 nightly
The price is $234 total per night from Dec 2 to Dec 3
$234 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (1,675 reviews)
Beautiful place! Great service!

Reviewed on Nov 15, 2025

Omni Louisville Hotel
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
$72 nightly
The price is $85 total per night from Nov 22 to Nov 23
$85 total
Nov 22 - Nov 23
Total with taxes and fees
8.8/10 Excellent! (962 reviews)
Room 220 was just what we required

Reviewed on Nov 15, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
See all 2,053 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Portland

United States Marine Hospital of Louisville

Though United States Marine Hospital of Louisville might be what brings you to town, perhaps you'll have a chance to explore more of Louisville while you are here.

United States Marine Hospital of Louisville

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 top-notch restaurants while you're in the area.

Kentucky Peerless Distilling Co.

Boone Square Park

Boone Square Park is just one of the places to see in Louisville, so why not enjoy the other things to explore during your travels? Experience the area's entertainment choices and lively festivals.

Boone Square Park

Things to do

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$22
per adult
90% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Lace, Lunacy, and Loss: Louisville Ghost Tours

$26
per adult
Lace, Lunacy, and Loss: Louisville Ghost Tours
Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
100% of travellers recommend
Kentucky Derby Museum - Admission with Guided Track Visit
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.