Top 9 Best Hip & Quirky Hotels in Portland

Have you heard of Portland? Chances are you have. Perhaps you have even heard the name ‘Portlandia’, a quirky sketch-based show that transported the town to mythical hipster heights. But the gentle ribbing of its inhabitants speaks much more to the varied lifestyles that occur in this west-coast haven.

The shifting fashions, cultural norms and industries; a celebration of our impermanence. How does it do this? Well, in a word: gentrification. This word has drawn negative connotations in recent years, but where Portland seems to differ is that it celebrates its past. Remembering and honouring its buildings and industries for what they were. And one area where this is done with aplomb is the bustling business of hospitality!

Join us as we take a tour of the top 9 best hip and quirky hotels in Portland, Oregon, available for you to book in 2022.

So what exactly makes a hip or quirky hotel? Is it the decor, or the history of the building? The style of the rooms, the location in town, or the amenities? This is what we will be highlighting on this whistle-stop tour of the great, the hip and the quirky!

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Is Portland Worth Visiting?

Portland was originally built as a port-town in the 1800s due to its perfect location on the banks of the deep Willamette river. As business took off in Portland the population grew, though it was still very much believed to be a frontier town. It wasn’t until the second world war that city began to boom. Chosen as a distinct location for shipyards building naval ships and aircraft carriers.

After the war, organised crime took hold amid fresh industry and the larger population brought about by the war effort. The town was full of gangsters forming protection rackets. In the mid 1990’s the dotcom bubble saw an influx of fresh young talent. Many people saw Portland as a great city with great access to nature, low cost of living and a burgeoning market of jobs in online industries and design.

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As such, Portland has had an interesting past. Now, it is very much positioned as a city that has only recently ‘found its feet’ as a centre for people looking to make a buck their own way. It has become the hipster scene full of artists and free-thinkers who want to create something new. A lot of this springs from looking at past cultural movements, taking elements and creating new and exciting scenes.

Some people find this too much like re-hashing the past. Others like us find it a cultural excavation and celebration of the old and new! But with the influx of free-thinkers and arty folks, came a veritable hotbed of cultural creativity. Indeed, some of the biggest names to come from Portland read like an alternative guide to creative greatness. Courtney Love, Matt Groening, Chuck Palahnuik. We could go on!

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Portland Today

Now, gangsters have been replaced with hipsters, and industry is going strong. Albeit of a different kind. Portland is full of fascinating finds. Quirky nooks, like the giant bookstore ‘Powell’s City of Books; Bars of wonder like the Multnomah Whiskey Library; famous gig venues like The Aladdin’s Cave and The Crystal Ballroom (which we will come to later); and the wonderful unrefined vibrancy of places like Mississippi Avenue in Boise, and the industrial-turned-hipster pearl district, where you can find the best breweries in town.

Take a cycling tour of the ‘city of bridges’, so-called for its staggering amount of bridges and the incredible levels of engineering acumen within. Trek out to Washington Park and take in the city panorama. Stay in China town, stomp the streets, grab a delicious coffee and nibble a tasty treat from Voodoo Donuts.

Do all of these things, but make sure you have somewhere comfy to stay at night! Somewhere quintessentially hip, or with a quirky swagger. There is no shortage of hip hotels in Portland.

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9 Best Hotels: Where to Stay in Portland

Yes tourism is a great money-spinner, and while we tour we need places to stay! So, Portland have given us a bevy of fun and interesting places to stay. Places where you can chill between explorations and soak up the ambiance of this quirky town. Hotels that capture Portlands multi-faceted charm, whilst marking its cultural past and present.

You might be wondering, where do celebrities stay in Portland? The Heathman Hotel gets an honourable mention, as not only is it one of the ‘go-to’ hotels for the rich and famous, it was also made more visible by its exposure in ‘Fifty Shades of Grey’. Whilst its not featured in this rundown, it is a very fine hotel for someone looking for a balance of elegance and eclectic style.

Rest assured: whichever of these 9 hip hotels in Portland that you choose to stay, you will feel like a rockstar, a film star of just a plain old A-grade hipster!

Hotel Vintage

Located in the southwest area of downtown, a walking distance from the Portland Art Museum, the Hotel Vintage offers luxury, though definitely with a quirky twist. As a larger boutique residence, dining is available at two delightful restaurants, and a games room also features for entertainment without leaving the hotel. It also boasts a great fitness centre and in-room spa service. Divine!

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These rooms are impeccable, ranging from the wood and chrome ‘Mad Men’ feel, to the more contemporary loft conversions, and colour-palettes in rich brown and cream, to bright white and reds. All rooms come with plush beds, a desk and flat screen TVs. Some suites even come with a balcony and a hot-tub!

For guests wanting the ultimate hip wedding at hotels in Portland, check out the Wine Cellar wedding venue on site! Certainly, this is one to note if you want that hipster-bougey charm with plush, luxury accents. It is also pet-friendly.

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The Staypineapple at Hotel Rose

This is a tremendous hotel for anyone who loves bright colours and quirky decor! Free wifi throughout the hotel, free biscuits and coffee in the lobby daily, and free rental of cruiser bikes. The restaurant and bar are beautifully decorated, and small enough to feel cosy.

Whilst the rooms are admittedly less over-the-top than the communal spaces and hotel lobby, every room features a Keurig coffee machine, a mini-fridge, flat screen TVs, and gorgeous fluffy bathrobes. All these features are bound to make this the comfiest stay ever.

The Rose Hotel is situated on the banks of the Willamette River, opposite the gorgeous Tom McCall waterfront park. This makes it a great stay for guests who want to be in the centre of the action.

McMenamins Kennedy School

Once an Elementary school opened in 1915, McMenamins Kennedy School now features 57 bedrooms which all have a signatures quirk. Some are converted from classrooms, with chalkboards still in tact. Others are formed from cloakrooms, and some are themed around an authors works!

Guests will be spoilt for choice with six bars and restaurants to choose from. And if you’d like a souvenir from your stay, you can pick one up at the Kennedy School gift shop! The decor is very much in keeping with its old-school (literally) beginnings, and the courtyard is a wonderful place to spend a few hours soaking up the sun and having a few drinks and a delicious meal. The Boiler Room bar is also a fabulous two storey affair with pool tables and a wide balcony set upstairs.

Located on the north east corner of town in the Concordia area, it is a little further out of the centre. But with the added beauty of the courtyard gardens, and the availability of local paid bikes, you wont have trouble getting around!

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Jupiter Hotel

Yet another converted building, this used to be a motor lodge before being converted into a chic, hip boutique hotel. The Jupiter combines modern minimalist design with pop-culture twists. The rooms are available in five styles, all plush and pet friendly! The best of course is the Dream Suite, which features floor to ceiling mirrors, bar and living area!

Located on the east side of the river, 20 minutes walk from Tom McCall waterfront park, the hotel owners state that the hotel’s “lush city vibes are a nod to Portland’s rich history of makers and creators”. We certainly cannot argue, and with a live music venue on site as well, this is perfect for those city loving tourists looking for a bit of true Portland-living. The Doug Fir Lounge is a great place to have a few drinks and take in the northern-states charm. Outdoor lounging areas with in-built fire-pits are a great place to cosy up if visiting in autumn! The Hey Love restaurant offers Portland charm with an exotic inspired twist.

Well, fusion is the name of this city’s game!

The Society Hotel

This is one of the best hip hotels in Portland for a couple of big reasons. One, its location near China Town is a perfect jumping-off point for exploring the city. Located on the west side of the river, just a few streets back from the waters edge, Voodoo Donuts is also close by for all your sugar needs!

Two, the hotel is very affordable both for private rooms and hostel-style accommodation with a luxury twist! Double rooms themselves are very cosy with a minimalist feel, whilst the dorm section of the hotel has a large number of beds contained in a large airy room set over two floors. Whilst this might sound less than enticing, but each ‘bunk’ is a self-contained sleep-pod. They are roomy, with extremely comfortable single beds, dedicated lighting and plug sockets, and a full-length curtain for hiding away when its time to sleep! There are also large lockers free to use to contain your things whilst out and about.

Renovated from its beginnings as a sailors lodge, the exposed brickwork and pale decor is beautifully in keeping with the local hipster aesthetic. Plus, the cafe and bar serves great coffee, fabulous food, and the rooftop chill-out space affords great views over the city. If you are looking for luxury on a budget, The Society Hotel is one for you!

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The Hoxton Hotel

For plush near Gatsby-esque luxury in the heart of Old Town, just a stones throw from the Society Hotel, look no further than the Hoxton. It has touches of the gangland history of Portland, but in a hip hotel. The bar Is beautifully decorated, featuring sleek interiors and large ornamental pieces. The cocktail menu is extensive and you will never tire of the view from the rooftop restaurant! The hotel has 3 restaurants and bars across 3 floors, all beautifully decorated in their own styles and colour scheme inspired by mid 1960s design, but with additional elements of the bygone eras of this town.

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The hotel rooms are very much in keeping with the decor throughout the hotel. Each room is beautifully rendered and create a sense of calm and peace. Large windows let the light in and cast the tasteful furnishings in a bright optimistic glow. You will honestly never want to leave this place!

Hotel deLuxe

One of the finest locations to stay in downtown Portland, this Hotel deLuxe is a masterclass in Hollywood glamour and charm. Open since 1912, the hotel has been decorated in keeping with the deco style of the era, though with some modern twists throughout. It also contains a multitude of cinematic references and plush furnishings to go with it! The hotel features a pop-up cinema showing movies by all the greats you could imagine, and maybe some you have never heard of.

All the rooms are light and airy, with creamy pastels and large soft beds. The best room, however, would be the Marlene Dietrich Suite. This features a beautiful view of the city and a wonderful 8 foot circular bed! Hollywood glamour indeed! All rooms include free wifi, and have a a ‘locally influenced honor bar’ as standard.

Guests can take afternoon tea in the delightful lobby, or take advantage of signature deLuxe cocktails in the Driftwood Room bar. Or have dinner in Gracie’s, the hotels plush restaurant. And, each Wednesday guests can enjoy tastings from local businesses. These can include everything from coffee roasters to breweries, wineries or distilleries. Even the odd food vendor will supply local fare for the discerning guest.

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The Tiny House Hotel

This is one of the most hip hotels in Portland, the Caravan – The Tiny House Hotel is to die for. It features an array of tiny, beautiful, and free standing properties for guests to stay in! Guests can choose from 5 little cabins, arrange around a beautifully put together communal space, replete with fire pit, comfy chairs and awning, and all the s’mores you can eat! Even vegans will be happy with animal-free marshmallows.

All rooms are wonderfully decorated in natural materials and pale colours, with wooden furniture and modern bathrooms. These ‘rooms’, which are more like small caravans, may be small, but they are perfectly formed and come with a kitchenette, full bathroom, sitting area and a bed built above the kitchen, accessed via ladder. This is not for those with accessibility issues, but is a wonderfully adventurous stay for those who like hotels with a marked difference!

The names of each lodging is unique, such as ‘The amazing Mysterium’ and ‘Kangablue’, and wonderfully out-there. It certainly gives a hint to what might lie beyond! Plus, everything you see within the rooms, and all amenities, are fair trade and locally sourced as much as possible. You wont find a TV or wifi inside, though each room is fitted with a hifi and connector for a smart phone or iPod.

McMenamins Crystal Hotel

The McMenamins Crystal Hotel is where all the action happens. Not only is this a world-class hotel, this is also contains tow historic music venues! Both the Crystal Ballroom and Lola’s room have shows year-round. So, if you want the soundtrack of your stay to be glorious live music, this is the one for you!

Yes this is certainly one for the music fanatics amongst us, and with three bars as well, you will feel totally at home. And the Zeus cafe is open all day serving breakfast lunch and dinner. All made with the finest ingredients sourced from the north west. So much so you could quite easily spend your whole trip inside the venue. Plus, you can make use of the incredible oddly shaped salt water ‘soaking pool’, where you can go to wash away all the days activities and relax before hitting a live show!

Each room at the hotel is inspired by one of the most notable shows in the venue’s history, with fun, mystic and downright odd eclectic decoration that will thrill the most avid of music fans. Guests can even book gig packages in advance!

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Hip Hotels in Portland: Where Will you Stay?

This concludes out whistle-stop tour of hip hotels in Portland. From divine luxury of The Hoxton Hotel, to the classic elegance of Hotel deLuxe. From the madcap mastery of The Tiny House Hotel, to the glorious live and musically inspired majesty of the Crystal Hotel. All have a unique flavour and flair! Certainly, this is a town who’s fractured beginnings and oddly-shaped past has borne a population of free-thinking outliers. People who are able to bring an intoxicating mix of cultural movements together to create something both luxurious and wildly different.

We hope you have found something that will suit your taste. At the very least, you are sure to be hungry for a visit to the west coast hipster capital of America. If you have a burning desire to visit, best share this with your nearest and dearest to inspire them to join you. this is a town best viewed with friends. And you are sure to come back a lot of stories to tell!

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James Ardimento has spent the last 12 years journeying around the globe ! With its precious experiences and tips he gained around Asia, South America, Europe and the US he is a precious asset for this blog and for its readers