Portland Vacations from $611

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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.
The Brown Hotel

The Brown Hotel

Downtown Louisville
$611
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,289 reviews)
The property was clean, and the bed was comfortable. I couldn’t really see why it would be considered a luxury hotel, other than really old furniture and antique looking like decor.

Reviewed on Sep 20, 2026

The Purple Martin

The Purple Martin

$803
per person
Dec 3 - Dec 6
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (2 reviews)
Amazing property… I would come back in a heartbeat!

Reviewed on Jun 19, 2025

The Grady

The Grady

Downtown Louisville
$662
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,005 reviews)
Louisville Marriott Downtown

Louisville Marriott Downtown

Downtown Louisville
$691
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Nothing to add

Reviewed on Sep 20, 2026

The Trail Hotel

The Trail Hotel

$673
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9.2/10 Wonderful! (318 reviews)
An amazing facility. Old Holiday Inn that has been totally updated with a Bourbon Trail vibe.

Reviewed on Sep 19, 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

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
A brown horse with a red halter, a person in a black shirt, and a crowd of people in the background.

Fairgrounds

1 out of top 10 points of interest in this area

While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.

Find hotels in Fairgrounds
A nighttime cityscape with a brightly lit bridge and a skyline featuring a prominent dome-shaped building.

St. Matthews

Major shopping destination with the fifth-largest mall in Kentucky, Mall St. Matthews, and smaller centers along Shelbyville Road. Don't miss the historic St. Matthew's Episcopal Church and Holy Trinity.

Find hotels in St. Matthews
A city skyline at dusk with illuminated buildings reflecting on the water.

Jeffersontown

Jeffersontown is known for its abundant dining options, and you can plan a trip to Jeffersontown Commons Shopping Center and Bluegrass Indoor Karting while you're in town.

Find hotels in Jeffersontown
A large, illuminated two-story house with a prominent front porch and a garage.

Old Louisville

Boasting Victorian architecture and the highest concentration of stained glass windows in residential homes, Old Louisville offers a walkable neighborhood with pedestrian-only streets, diverse dining options, and attractions like Central Park and the Conrad-Caldwell House.

Find hotels in Old Louisville

Portland Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$162 nightly
$191 total
Oct 4 - Oct 5
Total with taxes and fees
Galt House Hotel Trademark Collection by Wyndham
Holiday Inn Express & Suites Louisville Downtown by IHG

Holiday Inn Express & Suites Louisville Downtown by IHG

800 W Market St Louisville KY
Fully refundableReserve now, pay when you stay
$118 nightly
$139 total
Oct 4 - Oct 5
Total with taxes and fees
8.8/10 Excellent! (1,822 reviews)
"It was clean and the breakfast was pretty good. This is the first time I have stayed at a Holiday Inn Express in years but I would definitely stay here again."

Reviewed on Sep 20, 2026

Holiday Inn Express & Suites Louisville Downtown by IHG
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

830 Phillips Lane Louisville KY
Fully refundable
$110 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Crowne Plaza Louisville Airport Expo Ctr by IHG
See all 2,109 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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations
Gay Friendly Vacations
LGBTQ Friendly Vacations
LGBTQ Friendly Vacations
Adventure Vacations
Adventure Vacations
Vacations in Month
Where to go when
Where to go when
Honeymoon Vacations
Honeymoon Vacations
Mountain Vacations
Mountain Vacations
Fishing Vacations
Fishing Vacations
Adults Only Vacations
Adults Only Vacations
Waterpark Vacations
Waterpark Vacations
Scuba Diving Vacations
Scuba Diving Vacations
Yoga Vacations
Yoga Vacations
Cheap Vacations
Cheap Vacations
Solo Vacations
Solo Vacations

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.
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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 acclaimed theater scene and entertainment choices.
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Lannan Park Trailhead

You can take time to visit Lannan Park Trailhead during your travels to Louisville.
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Portland Museum

You can spend an afternoon browsing the exhibits at Portland Museum during your travels in Louisville. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
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Things to do

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$24
per adult
94% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

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

$129
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
See the sites that inspired movies and playwrights.

Loss, Lunacy, and Lace: Haunted Louisville Guided Ghost Tours

$26
per adult
Loss, Lunacy, and Lace: Haunted Louisville Guided 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.