Top 12 cool and unusual hotels in Portland

Ah, Portland! One of my favourite places in the USA. When I visited early last year I had the sensation I may just have found my spiritual home. Small and compact, not too far from the beautiful Oregon coastline, Portland epitomises everything which is good about the hipster scene. Bursting with cool style and character and a sense of hope and community it reminded me very much of London’s famous Camden Town circa the 1990’s. I was delighted to find myself surrounded by cool little cafe’s, chic and cheap vintage shops and good-natured, eco-minded hipsters with a heart. After a little scout around I found the charmingly unique Portland hotels also reflect the city’s progressive and idiosyncratic ideals. Here are my favourite cool, quirky and unusual hotels in Portland, Oregon to help you plan your fun and perfectly hip USA holiday…

Society Hotel – funky and historic budget accommodation

This is such a cool and characterful place. This splendid New York Style cast iron building is rich in maritime history – in its heydey it was a hotel for sailors and I can only imagine what kind of shenanigans occurred here…Nowadays The Society Hotel is a sympathetically restored budget boutique hotel, located right in the centre of downtown Portland in the Chinatown/Old Town area. There is a choice of rooms; hostel-style bunks or simple private rooms with shared bathrooms for affordability or ensuite suites for a bit of luxury. I loved the stripped down and exposed style of the hotel’s interior and the food in the on-site cafe was absolutely delicious… washed down with a craft ale in true Portland style, this place is a real find if you’re a funky budget traveller like me…!

The Heathman Hotel – elegant hotel made famous by 50 shades…

This option wouldn’t suit the budget traveller but if you want to splash out on a completely deluxe boutique experience, the Heathman Hotel is where it’s at! Situated in the heart of Portland, close to all the galleries, parks and museums the unique Portland hotel is second to none for old time elegance. Although arguably its most famous accolade is being the site of Ana and Christians first rendezvous in Fifty Shades of Grey! The boutique rooms are spacious and artfully designed and the intimate Tea Court Lounge offers delicious fine dining and live Jazz twice a week. The lovely award-winning historic hotel also offers an ‘Art of Sleep’ bed menu which allows guests to choose from a selection of sumptuous mattresses, a unique lending library for guests and a ‘pampered pets package’ if you also wanted to take a furry friend – delightful luxury option!

McMenamins Kennedy School – boutique kitsch coolness

This repurposed Art Nouveux era elementary school is a class of its own, literally! With half of its 57 boutique rooms maintaining their original classroom character and the other half sporting literary themes – the McMenamins Kennedy School radiates an unusual vintage cool. Thankfully craft beer and freshly roasted coffee replace school dinners in this hotel. Guests can enjoy the house brew in the Concordia Brewery (formally the little girl’s room!) listen to excellent live music in the on-site venue and munch on delicious sustainably sourced grub in the Courtyard Restaurant. After a day exploring all the Portland landmarks, you can unwind in the saltwater pool or combine homegrown pub fare with movie magic on the auditorium cinema screen! A truly unique and fun Portland hotel experience.

Ace Hotel – arty and so very Portland…

This refreshing little chic and funky Portland hotel is an affordable option without compromising on style and comfort. Based in a historic building in downtown Portland, The Ace is close to all the sites and on plenty of public transport links. The spacious rooms are lovingly decorated by local artists and you can enjoy home-cooked locally sourced food and drink in the Clyde Common restaurant and bar. If you fancy exploring the city on two wheels there are bikes to borrow or you can even rent a bespoke handmade bike created for the hotel by artist Jordon Hufnagel. There are plenty of cosy communal spaces where you can chill out with fellow travellers and also make sure you take advantage of the gorgeous vintage photo booth to capture some old style holiday memories!

  • Prices from $140 per night
  • To book, check prices or availability for The Ace Hotel

Hotel Vintage – gorgeous elegant boutique hotel

The Pearl district is a historically industrial neighbourhood close to downtown Portland whose old warehouses and breweries have been reclaimed and resurrected by artists and in the heart of Pearl is where you’ll find this very cool Portland hotel. Hotel Vintage is a pioneering upscale hip boutique hotel which features delightful design details such as a floating staircase and a bunch of grapes chandelier as well as an adult games room and two wonderfully contemporary eateries. The Pazzo restaurant offers local wines and cream of the crop Italian cuisine, while the casually cool Bacchus Bar holds delicious craft beers and wines amongst old school arcade games and pool. Priding itself on its gastronomy, the hotel also offers urban tasting sessions in its exquisitely designed lounge room. This is kitsch cool comfort at its finest!

  • Prices from $170 per night
  • To book, check prices or availability for Hotel Vintage

Jupiter Hotel – very cool retro chic

For modern travellers, cultural creatives and anyone who lives outside the box’ the Hotel Jupiter, located in the hip Burnside area of Portland, may be the place for you. If you want to party the night away you can stay on the bar side of the hotel, right next to the Doug Fir Lounge and Restaurant, this award-winning small venue offers excellent food, beer and live music so you can rock ’til the small hours! For a more peaceful stay choose a room on the chill side. All rooms feature chic 1950’s American dream inspired décor and everything you need for a very comfy stay. The hotel is dedicated to supporting local artists and small businesses and the first Friday of every month it hosts a ‘reception for the artist’ event where you can mix with local artisans and explore multi-sensory art forms with like-minded people. An ideal hip mid-range Portland hotel for the streetwise urban traveller, this is contemporary culture at its best!

  • Prices from $120 per night
  • To book, check prices or availability for Hotel Jupiter

McMenamins Crystal – the funky rock n’ roll hotel

Enjoy downtown Portland at its Rock ‘n’ roll finest at this quirky Portland hotel inspired by The Crystal Ballroom’s extensive musical history. The décor in each of the 51 rooms at the McMenamins Crystal Hotel is influenced by one of the stand out show’s at the Ballroom – from Blondie to The Flaming Lips, local artists and fans have done their best to capture the atmosphere generated by these music icons. With The Crystal Ballroom just across the road, you can even become part of the story! Like all Mcnemanin Hotels this one is situated in a historic building; it has its own venue and it serves up food and brews made from only the finest Northwest ingredients. For all you music lovers out there this very cool Portland hotel even offers limited room and gig packages that are well worth a look!

Staypineapple at Hotel Rose – colourful kitschy chic

Staying at a Staypineapple hotel is always a thoroughly decent experience and Rose Hotel is no exception. The ultra-comfortable rooms offer a choice of views out over city, waterfront and park. I chose the city as I love a good cityscape and I was not disappointed. My room was spacious and super comfy, well designed with a touch of retro flair and a wonderful walk-in rain shower that I didn’t want to get out of. As always there were cool communal spaces to hang out in…. I especially adored the massive fireplace and the craft cocktails. I had a coffee maker, iPhone dock/ Bluetooth speaker, big TV and super comfy bedding in my room and the friendly staff were always on hand to help if I needed it…however the hotel had been so thoughtfully equipped I only needed to chat to the staff when I was looking for local things to do. They had plenty of ideas for me and I loved hiring one of the hotel’s vintage yellow cruiser bikes and heading off for adventures – definitely an Instagram moment! A thoroughly cool experience all round, great work Staypineapple!

Hotel Modera – stylish retro/modern boutique

Situated right in the middle of the arts district Hotel Modera embraces Portland’s unique brand of style and spirit offering a tranquil, pet-friendly stay in the heart of town. Blending clean sleek lines and welcoming warmth The Modera offers everything required for a refined and relaxing stay. The hotel has a zen interior courtyard complete with fire pits and the city’s first-ever living wall. What’s more, you can begin your exploration of Portland’s renowned food scene right here at the hotel’s own Nel Centro a fine dining experience engineered by celebrated Portland chef and restaurateur, David Machado. If unique culture is your thing, this may be your perfect hotel!

  • Prices from $140 per night
  • To book, check prices or availability for Hotel Modera

Sentinel Hotel – creative and historic luxury

The luxurious Sentinel Hotel is housed in a historic terracotta building in downtown Portland is a place where creative thinkers, artists and entrepreneurs can lay their head and be inspired. The wonderful interior is a fusion of old-time luxury and contemporary ideas with black and white prints of inspirational people and thoughtfully curated local art. I stayed on the top floor and had access to the lovely ‘Room at The End Of The Hall’ a place that deliberately inspires creativity. The food in the hotel’s two restaurants was quite delicious and I really admired the green attitude of the Sentinal, which has its own beehives on the roof to supply the hotel with honey! This is a really innovative combination of luxury and free thinking and a great place to stay when visiting this brilliant and quirky city. 

  • Prices from $170 per night
  • To book, check prices or availability for Sentinel Hotel

Hotel Monaco – unique eco-luxury boutique

Hotel Monaco wears eccentric eco-chic like a comfortable shirt, mixing eclectic furnishings and cosy vintage décor with heaps of personality… sort of like a microcosm of Portland itself. The on-site Red Star Bar boasts creative cocktails and one of the largest whisky selections in downtown as well as microbrews and local wines from the Willamette Valley. The Red Star Tavern serves up innovative dishes compiled from local organic ingredients. To top it off the beautifully unusual Portland hotel is situated in the wonderfully cosmopolitan Pearl District.. a shining example of urban renewal at its best!

  • Prices from $200 per night
  • To book, check prices or availability for Hotel Monaco

The Lion and The Rose – guesthouse with bags of nostalgia

What can I say, this is no ordinary guesthouse, this is a lovingly refurbished Victorian mansion that takes guests back to a bygone era. For nostalgic souls like me, The Lion and the Rose is just perfect… it is also opulent and luxurious with no expense spared on comfort and amenities and possibly the best breakfast I have ever eaten! I stayed in the smallest room, The Avandel, but was blown away by the attention to detail and the perfect period touches. My bathroom was just across the hall but it was exclusively mine and wow, what a bathroom! The porcelain tub stood on golden lions feet upon a polished marble floor and was covered in delicately painted flowers… the floral motif was continued in the drapes, tiles and wallpaper… some may have found it a bit of a floral overload but for me it was heavenly. After a few days reading on the wraparound porch and working my way through the many blends of tea on offer I was ready to buy myself a cotton and lace nightdress and take up needlework – for lovers of history and nostalgia this place is an absolute dream. 

Hotel Vintage – gorgeous upscale design hotel

If you love wine then you really don’t want to miss this place. As I walked in Hotel Vintage I felt like I was encased in a beautiful mellow bottle of vintage red. The décor is so warm and draws from wine for inspiration with predominant colours of cork, deep reds and ochres and rich greens. Really beautiful! A true boutique too with no two rooms the same and every room decorated for a different Willamette Valley wine. I stayed in a gorgeous skyloft room and felt like I was on top of the world – my room was bright and spacious with lovely touches like a cork wall behind the bed and a solid wood work table. On arrival I found a bottle of wine waiting for me and I thoroughly enjoyed the nightly social hour/wine tasting whilst I was there too. There was plenty of in-house communal spaces and food and drink which was lovely…I made the most of the games room and worked my way through the local wines at the Baccus Bar. I also got a few credits for the delicious Pazzo restaurant when I didn’t use housekeeping. Lovely to be rewarded for little things like that! A great experience in the heart of vibrant Portland, the only problem is I didn’t want to leave…

  • Prices from $150 per night
  • To book, check prices or availability for Hotel Vintage

Hotel Deluxe – old school Hollywood glamour

For a film buff like me, Hotel Deluxe is a dream exuding the glamour of Hollywoods golden years from every wall. Not an alcove remains untouched by the silver screen as the hotel is adorned with a magnificent collection of film stills from the 1930’s through to the 1960’s and each floor is a homage to a director, actor or era in cinema from Hitchcock to Gene Kelly, from Brando to Bardot… this place has them all. It also has a pop-up cinema showing semi-impromptu classics accompanied by craft beer or an elegant cocktail! The whole place is beautifully designed with soft luxurious fabrics and colours, polished wood and timeless elegance. My room was a calm oasis of cream and pale green that brought to mind Parisian luxury in the 1940’s. Beautiful, tasteful and vintage. There are loads of communal spots and plenty of options to eat and drink and as a real treat I enjoyed Afternoon Tea in the opulent lobby whilst I was there. It was exquisite of course like everything else in this hotel. If you moon after Marilyn or wish you could wear a headscarf with the same finesse as Hepburn, this place will make you feel like a movie star, at least it did for me!

  • Prices from $170 per night
  • To book, check prices or availability for Hotel Deluxe

The Inn@Northrup Station – fun, colourful and funky

This offbeat psychedelic Portland hotel will blow your socks off if you love colourful retro kitsch! The Inn@Northrup Station is situated in bustling NW Portland close to boutique shopping, Aladdin’s cave of vintage goodies, craft breweries and cafe’s galore! It’s right on the eco-friendly streetcar line, so travelling in and out of downtown couldn’t be easier. Like all cool Portland hotels worth their salt you can enjoy contributions from local artists and delicious house roast coffee in the hip street side bar, or interact with the street scene below from your own balcony or the communal rooftop terrace. You can help yourself to sweet treats from one of the giant candy jars and soak up the unique spirit of NW Portland, you will definitely leave significantly hipper than you arrived!

Hotel Eastlund – retro design boutique

Situated in the heart of the bustling eastside of the city this boutique design hotel was a real find. The interior of Hotel Eastlund sports a gorgeous and sophisticated 1960’s esque design full of geometrical shapes and 1960’s chic shades. There is an amazing rooftop restaurant with spectacular views over the city and a delicious beer-centric menu to die for and also an artisan bakery onsite! I stayed in a King room and it was spacious, bright and clean with an enormous bed and some cool retro artwork on the walls, my only gripe was the down bedding which I am horribly allergic to but the ultra friendly and efficient staff changed it over for me no problem. An awesome place from which to explore everything cool and unusual that Portland has to offer!

  • Prices from $160 per night
  • To book, check prices or availability for the Hotel Eastlund

The Nines Hotel – fabulous designer opulence

Hotel Nines is seriously a masterpiece in design. Walking into the grand open plan space, cleverly sectioned off into smaller, cosier alcoves without impacting the flow really took my breath away. So much thought has gone into this interior…from the wonderful artwork supplied by the local art college to the innovative play on light and space that characterizes The Nines…it really is a pleasure just to be in it! Luxury and elegance triumphs throughout, a perfect homage to Meier & Frank who brought the building to life in 1909 as their flagship department store and headquarters. Absolute luxury all round and the service to match it, the dining is not too shabby either. Not a budget stay but it is worth every penny if you want a real treat!

  • Prices from $150 per night
  • To book, check prices or availability for Hotel Nines

Hotel Aloft – the coolest airport hotel around

Forget every preconception you have about airport hotels and give this one a go because it’s awesome! Yes, it’s too big to be boutique but it is certainly an innovative design hotel full of all the creature comforts and lots of hip little Portland twists! I particularly enjoyed the bar at Hotel Aloft which had live music from the coolest emerging local artists almost every night I was there… and the cocktails were good too! The room was bright, bold and comfortable and the hotel amenities were excellent, a really pleasant surprise all round and thoroughly recommended!

  • Prices from $150 per night
  • To book, check prices or availability for Hotel Aloft

Bluebird Guesthouse – cute and cosy arts & crafts home

The BlueBird Guesthouse is a lovely balance between a Hotel/ B&B/Self Catering Cottage situated in a sympathetically restored Arts and Crafts house in the Division/ Clinton Neighbourhood…within walking distance of the cool retro boutiques and cafes of Hawthorne and a short bus/car/bike trip into Downtown I loved this place which was cosy, homely and communal and encouraged guests to get together and be social just by its size and layout. I stayed for a week and met some great friends and was really sad to leave the peace and comfort of my little room. Each room was named after a great American writer and my room was Ken Kesey…Thankfully it didn’t emulate the conditions of One Flew Over The Cuckoo’s Nest but was instead a light, bright and tranquil attic room with a skylight looking up into the stars. I really recommend this place if you are travelling alone on a bit of a budget, want to meet folks along the way but don’t want to be stuck in a noisy mixed dorm room. This is a home away from home but book early as rooms are taken way in advance!

Apartment Options

Pearl Apartments – modern, swish and spacious

The Pearl Apartments are a great alternative to a regular hotel stay where you can chill out with a group of friends and enjoy everything the city has to offer. We absolutely loved staying in the bright, airy and ultra-modern apartment which had an abundance of light and space and a fab contemporary vibe. On the doorstep was the fantastic Pearl District, a positive treasure trove of boutique shops and eateries in the heart of the old industrial centre and having our own apartment gave us the opportunity to cook up our own recipes using some of the tasty local produce available in the city’s numerous delis. The apartment was home to six of us for a week and it was such a treat we plan on making it an annual holiday! A new way of experiencing Portland and one I can heartily recommend!

Stay Alfred Apartments – modern, cosy and trendy

If you like a bit of freedom and all the creature comforts of modern living then Stay Alfred Apartments could be a good option for you. I stayed here with friends and it was pretty ideal! Right in downtown Pearl district and pretty swanky with amazing views over the city, a communal roof terrace and a gym at our disposal! Gorgeous modern décor and lots of space…a real treat coming from a tiny English home! It was great to stay self-catering too as Portland is chock full of foody hangouts and it was such a pleasure to hunt out culinary delights for our evening meal. A luxurious alternative to hotel living and thoroughly recommended.

More cool, quirky and unusual hotels in Portland

Portland cool and unusual

  • HI-Portland Hawthorne District – An eco-minded hostel located in the Hawthorne district housed in a historic 1909 Craftsman house from $40 per night.
  • Hotel Westin – A luxury boutique hotel located close to all the attractions from $190 per night.
  • Hotel Lucia – Set in a 1909 landmark, this chic downtown Portland hotel offers classy decor and excellent service from $170 per night.

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Beth was born under a wandering star, with drama in her veins and ink in her pen. After stints studying theatre in Dublin and Utrecht she used her creative streak to see as much of the world as she could on as little money. She toured Italian Schools with a children’s theatre troop, lived as an au-pair in both Rome and Washington DC, explored the British countryside, worked her way through much of Europe, Salsa’d in Cuba and road tripped down America’s west coast where she discovered her spiritual home; Portland, Oregon. In between adventures she resides peacefully with her cat and ukulele amid the misty valleys and rolling hills of beautiful South Wales.


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