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Portland Holidays

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Where to stay in Portland

Find the best Portland areas for the activities you enjoy most.
A street with a modern building featuring large murals, parked cars, and a café with outdoor seating.

Pearl District

The Pearl District offers an artistic haven where warehouses have transformed into Portland's premier galleries and design studios. Wide pavements lined with outdoor sculptures lead to Jamison Square's interactive fountain. Powell's City of Books anchors this creative area filled with craft breweries and farm-to-table restaurants. Red brick industrial buildings contrast with sleek glass condominiums to create a sophisticated urban feel. Hop on the MAX Light Rail or Portland Tram to explore easily. The district buzzes with energy during First Thursday art walks when galleries stay open late.

A theater marquee with 'Portland' and 'An Evening with Crosby, Stills & Nash' written on it.

Downtown Portland

City centre Portland pulses with energy where culture and commerce meet along the Willamette River. The Portland Art Museum and cultural venues anchor the arts district. Pioneer Courthouse Square hosts year-round events as the city's living room. Food carts serve global flavours beside sleek office towers. Explore the Pearl District's galleries and boutiques housed in converted warehouses. MAX light rail stations make getting around simple without a car. Tom McCall Waterfront Park offers peaceful riverside paths perfect for morning jogs or sunset strolls.

A street with vintage shops, a dog walking, and people walking.

Nob Hill

Portland's Nob Hill area captivates visitors with its tree-lined streets and historic charm. Victorian and Craftsman homes stand proudly alongside hip boutiques and artisanal cafes on NW 23rd Avenue. This trendy district attracts creative types seeking Portland's celebrated food scene. Explore local landmarks like the Trevett-Nunn House or catch a show at Mission Theatre. The area offers excellent walkability with convenient tram stops throughout the area. Forest Park's lush wilderness begins at the neighborhood's edge, providing a perfect nature escape just steps from urban amenities.

A modern building with a glass facade and a curved entrance.

Lloyd District

The Lloyd District buzzes with Portland's biggest events at the Moda Centre arena and Oregon Convention Centre. Basketball fans flock here for Trail Blazers games while concert-goers and convention attendees fill its wide streets year-round. Former industrial buildings now house creative studios and art galleries throughout the area. Getting around couldn't be easier with multiple MAX light rail stops and tram service connecting you to city centre Portland. Holladay Park offers a green retreat between shopping at Lloyd Centre mall and catching sporting events. The nearby Willamette River and Eastbank Esplanade provide scenic urban pathways for walking or cycling.

A river with a bridge, a red building with 'OMSI' on it, and a modern glass building in the background.
Photo by Glenn Miller
Open Photo by Glenn Miller

Central Eastside

Portland's Central Eastside tells a fascinating storey of industrial spaces reborn as artistic havens. This creative district houses art galleries and design studios in converted brick warehouses alongside craft breweries and hip cafes. Colourful murals and street art brighten the urban landscape. The area offers unique experiences from the Portland Night Market to OMSI's interactive exhibits. Walk along the Willamette River or explore Distillery Row for locally-made spirits. With several metro stops nearby, visitors can easily connect to city centre while enjoying this quirky, alternative slice of Portland.

Discover the most popular places to visit in Portland

The Moda Center with a clear sky, trees, and a pedestrian area.

Moda Center

8.8/10 (3,362 reviews)
Portland's premier indoor arena hosts NBA's Trail Blazers and major concerts in a space designed for perfect acoustics. Arrive via MAX light rail to avoid parking challenges during game nights.

What to do in Portland

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

S$103
per traveller
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
See all activities in Portland

Portland Hotel Deals

Exterior

Hyatt Regency Portland at the Oregon Convention Center

Hyatt Regency Portland at the Oregon Convention Center
4.0 star property
2.1 km from Portland (and vicinity)
9.4 out of 10, Exceptional, (1,752 reviews)
"Amazing place."
The price is S$225
includes taxes & fees
23 Aug - 24 Aug
Hyatt Regency Portland at the Oregon Convention Center
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.
See all properties in Portland

Frequently Asked Questions

How much does a Portland holiday package cost?

You'll find cheap prices on Expedia for your Portland getaway. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Portland costs.

What are the cheapest months to go to Portland?

If you're hoping to snag a cheap Portland holiday package, consider planning a trip in December, January and February. You'll generally find better rates on airfares and hotels during these months — ideal for a budget-friendly getaway.

How many days is enough for Portland?

We'd recommend booking a Portland holiday for at least 2 days. This will allow you plenty of time to visit popular sights including Portland Art Museum and Keller Auditorium, and explore neighbourhoods like Downtown Portland and Lloyd District. You might even be able to slot in a day trip (or two) outside of Portland.

Is it worth booking a holiday package to Portland?

Portland has all the ingredients you need for an amazing trip — cycling, nature and distilleries and craft breweries are just the start. Whether you want to visit attractions such as Moda Centre and Oregon Zoo, or take the road less traveled, you'll find plenty to explore on your Portland holiday.

How to find the best Portland package deals?

Use Expedia's filters to help you find some of the best Portland package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Portland package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.

Is it cheaper to book a Portland holiday as a package?

You can enjoy significant savings on your Portland break by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a holiday package to Portland?

If you've got your Portland holiday dates locked in, book as early as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.

How to plan a trip to Portland?

  1. Pick your travel dates: What you'd like to do in Portland and your favourite season will help you decide when to go.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Portland.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to get to in Portland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Portland holiday package.

Book with confidence

Things to do in Portland

Portland is perfect for family-friendly, outdoor, and urban vacations, offering a range of activities such as engaging arena entertainment, vibrant shopping malls, and local centres. Visitors can explore adventure options like paddle trips, enjoy picturesque strolls through scenic parks, and relax in inviting picnic areas, making it an ideal destination for those seeking both excitement and tranquillity.

Shopping

Experience the vibrant shopping scene in Portland at the Streets of Tanasbourne Mall, offering a mix of entertainment and family-friendly vibes. Visit the Portland Saturday Market for local crafts and city atmosphere, or explore Pioneer Place for a blend of business and leisure in a bustling environment.

Recreation

Broadway Rose Theater Company offers an enchanting blend of romance and culture with captivating performances that uplift the spirit. For sports enthusiasts, Sckavone Stadium provides an energetic atmosphere filled with excitement. Meanwhile, McMenamins Crystal Ballroom showcases vibrant music events, creating a lively backdrop for entertainment lovers.

Adventure

Experience the thrill of high-speed racing at Portland International Raceway, where the excitement of motorsport comes alive. For a breathtaking view of the city, take a ride on the Portland Aerial Tram, offering stunning vistas. Enjoy family-friendly fun at Oaks Amusement Park, packed with rides and games for all ages.

Nightlife

Portland's nightlife is vibrant and diverse, with Tigard Bowl offering a unique blend of bowling and entertainment. Enjoy a night of friendly competition with friends, followed by drinks and dancing at nearby bars, where local craft beers and cocktails create a lively atmosphere.

Find the best attractions in Portland

Portland offers a delightful blend of family-friendly, outdoor, and urban experiences, making it an ideal destination for a vacation. Visitors can explore popular attractions such as urban parks, modern universities, and event venues, all of which cater to diverse interests and provide a vibrant city atmosphere. Whether you're seeking adventure in nature or urban exploration, Portland has something for everyone to enjoy.

  • Portland State University: Immerse yourself in the vibrant atmosphere of Portland State University, a modern educational institution that embodies the city's dynamic spirit. Enjoy its urban campus, where you can explore green spaces, striking architecture, and the buzz of student life.
  • Veterans Memorial Coliseum: Experience the thrill of live events at Veterans Memorial Coliseum, a hub of entertainment that caters to families and visitors alike. From concerts to sports, this arena offers an exciting venue for a memorable outing.
  • Oregon Museum of Science and Industry: Delve into the wonders of science and technology at the Oregon Museum of Science and Industry. With engaging exhibits and interactive displays, it's a perfect destination for families seeking a fun and educational experience.

Best time to go to Portland

The best time to visit Portland is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with moderate rain.

Tips to save on your trip to Portland

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Portland.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Portland.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.