Portland Vacations
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Where to stay in Portland
Downtown Louisville
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.
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.
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.
Fairgrounds
While visiting Fairgrounds, you might make a stop by sights like Freedom Hall and Kentucky Kingdom.
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.
Discover the most popular places to visit in Portland
What to do near Portland
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Portland Hotel Deals
Hampton Inn New Albany Louisville West
Hampton Inn New Albany Louisville West"The breakfast was the best! The room was nice. This isn't a place for scenery which isn't their fault but its not somewhere to try and see the river or have scenic trees outside the window. The toliet was loud when you flushed which woke me up when my husband went to the bathroom in the middle of the night. Overall though this was a good place to stay. I felt safe and would stay here again."
Comfort Inn & Suites Clarksville - Louisville North
Comfort Inn & Suites Clarksville - Louisville North"Parking is shared with the surrounding hotels, beware. Checking in was easy and the staff pleasant. Room was very clean and nicely decorated. Breakfast was lackluster and not kept warm properly. They ran out of both coffees and had no creamer available."
Cambria Hotel Louisville Downtown-Whiskey Row
Cambria Hotel Louisville Downtown-Whiskey Row
Hampton Inn Louisville Downtown
Hampton Inn Louisville Downtown"Room was very clean"
Hilton Garden Inn Jeffersonville Louisville North
Hilton Garden Inn Jeffersonville Louisville North
"So nice"
Frequently Asked Questions
How much does a Portland vacation package cost?
Get your credit card ready, because a trip to Portland starts from only . When you combine your flights, hotels and more into a vacation package, you'll score the best bargains.
How do I get a cheap travel package to Portland?
Browse and book everything in the one place with our Portland vacation packages. You'll find deals on hotels, flights, tours and more that'll keep your wallet happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 hotel options all over the world to select from, you have countless opportunities to mix and match your own way.
Where should I stay in Portland?
Visitors come from all corners of the globe to see Churchill Downs and Muhammad Ali Center in Portland. Stay near these must-see attractions to make sightseeing a breeze.
How far in advance should I book my Portland vacation?
While not all airlines advertise ticket prices early, you can normally look up international flights on Expedia up to a year in advance. This is when you'll score some fantastic bargains. If you're booking last minute, you could still be in luck. Discounted prices occasionally emerge just weeks prior to departure.
What does an Expedia Portland travel package include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply choose your favorite bundle and get access to great discounts. Once you've made your booking, add on some tours and activities and watch your savings stack up. When it comes to creating your Portland break, you're the boss!
What should I know before booking a Portland travel package?
A travel package can be easier on the wallet than individually booking everything you need for your trip. For example, combine your hotels, flights and rental cars and save big. Whatever your vacation goals are, you'll find a package to suit your budget.
Can I choose my airline with a Portland Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines throughout the world, so you have options galore when creating your Portland adventure.
If I'm not able to travel, can I cancel my Portland vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can cancel or change your Portland vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to learn more.