Portland Vacations from $253

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Embassy Suites Louisville East

Embassy Suites Louisville East

3.5 out of 5
Price was $362, price is now $253 per person
$253
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (1,003 reviews)
Large room ; Friendly staff ; very clean room ; pet friendly hotel

Reviewed on Sep 29, 2025

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

5 Bd/3 Ba-Near Expo/UL/Fair/YUM/Zoo

3 out of 5
Save 100% on your flight
Price was $1,257, price is now $886 per person
$886
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
No reviews
Hilton Garden Inn Louisville Airport

Hilton Garden Inn Louisville Airport

3 out of 5
Fairgrounds
Price was $370, price is now $271 per person
$271
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (1,008 reviews)
Across the street from Kentucky fairgrounds/Kentucky Kingdom, great location if you're attending music festival.

Reviewed on Sep 23, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $340, price is now $253 per person
$253
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
8.8/10 Excellent! (821 reviews)
We stayed here for the Louder Than Life festival. Easy check in, room was nice size and very clean. Staff we encountered the entire weekend were very friendly and courteous. We did have an issue as our air conditioning unit stopped working. Maintenance was super prompt and friendly. They had to swap in a new unit which only took about 20 minutes total to diagnose and replace. Amazing really. Will definitely stay here again!

Reviewed on Sep 30, 2025

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
Downtown Louisville
Price was $370, price is now $276 per person
$276
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Louisville (SDF)
9/10 Wonderful! (3,617 reviews)
Everything about the Galt House is wonderful!!

Reviewed on Sep 30, 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

3 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
$137 nightly
The price is $161 total per night from Nov 1 to Nov 2
$161 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (3,658 reviews)
"Very happy with my stay at The Galt House. We will definitely be back! 💖"

Reviewed on Sep 29, 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 Oct 19 to Oct 20
$234 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,623 reviews)
"Upscale stay, beautiful property, and great location! We were able to walk to so many great restaurants and the hotel really made a great experience for our first time in Louisville. Will be returning!"

Reviewed on Sep 21, 2025

Omni Louisville Hotel
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd, Louisville, KY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Oct 2 to Oct 3
$140 total
Oct 2 - Oct 3
Total with taxes and fees
9.4/10 Exceptional! (1,485 reviews)
"My room and the staff were absolutely amazing. This is my second time staying at this hotel and it never disappoints. One thing that I didn’t realize is that you have to request housekeeping services if you are staying for several days. No fault of the hotels though. I just didn’t know. However, ..."

Reviewed on Oct 1, 2025

Derby City Gaming & Hotel - A Churchill Downs Property
See all 2,008 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

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.

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

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 great live music and entertainment choices.

Boone Square Park

Things to do

Kentucky Derby Museum - Admission with Guided Track Visit

Kentucky Derby Museum - Admission with Guided Track Visit

$22
per adult
Kentucky Derby Museum - Admission with Guided Track Visit
Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

$32
per adult
Derby City Ghosts: Louisville Hauntings Tour
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories

$15
per traveler
Smartphone-Guided Walking Tour of Downtown Louisville Sights & Stories
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.