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 (in no particular order)…

McMenamins Kennedy School – boutique kitsch coolness

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Built in 1915, this repurposed Art Nouveux era elementary school is a class of its own, literally! With half of its 57 individually designed boutique rooms maintaining their original classroom character and the other half sporting literary themes – the popular and exceptionally rated 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 outdoor swimming 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…

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

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 vibrant beating heart of the city), the highly rated The Ace Hotel is close to all the sites and on plenty of public transport links. The spacious rooms are lovingly decorated by local artists but still come complete with free WiFi, minibars and flat-screen TVs 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 – including a funky onsite cafe and multiple cool restaurants – where you can chill out with fellow travellers, play a vinyl record or two or take advantage of the gorgeous vintage photo booth to capture some old style holiday memories! Wonderful!

Jupiter Hotel – ultra cool retro chic

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

For modern travellers, cultural creatives and anyone who lives outside the box’ the highly rated Hotel Jupiter, located in the hip and happening Burnside area of Portland (a 5-minute drive from Downtown), 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, free-WiFi, flat screen TVs and everything else you need for a very comfy – and trendy – Portland stay.

As well as a cool 24-hour art gallery and a contemporary courtyard patio with a trendy fire pit, 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!

Hotel Vintage – gorgeous elegant boutique hotel

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Located just half a mile from Governor Tom McCall Waterfront Park on Willamette River (in the lively Downtown SouthWest area an 11-minute walk from the Portland Art Museum) is where you will find this very cool Portland hotel. The 4-star exceptionally rated 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.

The chic guest rooms are equally as fabulous with flat-screen TVs, minifridges and upgraded rooms come with hot tubs, balconies or even blissful outdoor hot tubs. As well as welcoming pets and offering a modern 24-hour fitness centre, the gorgeous Portland abode prides itself on its gastronomy and offers urban tasting sessions in its exquisitely designed lounge room. This is cool kitsch comfort at its finest!

McMenamins Crystal – the funky rock n’ roll hotel

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Enjoy downtown Portland at its Rock ‘n’ roll finest at this quirky Portland hotel inspired by The Crystal Ballroom’s extensive musical history. Set in a building built in 1911, the décor in each of the 51 rooms at the much loved and highly rated McMenamins Crystal Hotel is influenced by one of the standout 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!

The wonderfully eclectic rooms are fabulous too and with the music theme running throughout the hotel, the vividly coloured rooms are each named after a well-known musician and come with fantastic city views and private bathrooms. Other very cool features include pets and children under 6 being able to stay for free, an indoor swimming pool and a wonderful art-gallery – music themed of course. Like all McMenamin 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. Music lovers out there will, of course, adore this very cool Portland hotel even offers limited room and gig packages that are well worth a look!

Sentinel Hotel – creative and historic luxury

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

The luxurious 4-star exceptionally rated Sentinel Hotel is housed in a historic terracotta building dated from 1909 in the heart of downtown Portland (set directly at a streetcar stop) 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 20th-century local art. I stayed on the top floor which had beautiful city views and had access to the lovely ‘Room at The End Of The Hall’ a relaxing lounge that deliberately inspires creativity. When I wanted to step up a gear I headed to the modern 24-hour gym. 

The food in the hotel’s two upscale restaurants was delicious and I really admired the green attitude of this hip Portland hotel – it even has its own beehives on the roof to supply the hotel with local honey! The elegant pet-friendly rooms offer free Wi-Fi and flat-screen TVs and opt for a flat screen and you’ll find cosy fireplaces too. 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 $130 per night
  • To book, check prices or availability for Sentinel Hotel

Hotel Eastlund – stylish retro design boutique

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Situated in the heart of the bustling eastside of the city (1.5 miles from Pioneer Courthouse Square and 3 miles from the Portland Japanese Garden), this boutique design hotel was a real find. The interior of the 4-star exceptionally rated Hotel Eastlund sports a gorgeous and sophisticated 1960’s esque design full of geometrical shapes and 1960’s chic shades.

The chic and colourful rooms come with free Wi-Fi, flat-screen TVs, and sublime city views and upgraded rooms offer extra rooms and soaking tubs. There is also an onsite shop, fitness centre, an amazing rooftop restaurant with spectacular views of the city and a delicious beer-centric menu to die for and also an artisan bakery onsite as well as a wine bar! I personally stayed in a King room and it was spacious, bright and clean with an enormous bed and some cool retro artwork on the walls, which I couldn’t fault. An awesome place from which to explore everything cool and unusual that Portland has to offer!

  • Prices from $115 per night
  • To book, check prices or availability for the Hotel Eastlund

Staypineapple at Hotel Rose – colourful kitschy chic

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Staying at a Staypineapple Hotel is always a thoroughly decent experience and the highly rated Rose Hotel is no exception. Located in the downtown heart of the city (one block from a MAX light rail station), the ultra-comfortable rooms offer a choice of views out over city, waterfront, and park. My room was spacious and super comfy, well designed with a touch of retro flair and kitsch cuteness, an ergonomic chair 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.

In this unique Portland stay I had access to the gym, freebie coffee and cakes in the afternoon and superb in-room amenities such as an 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 with the staff when I was looking for local things to do. They had plenty of ideas for me and I loved the hotel’s vintage yellow cruiser bikes and heading off for adventures – definitely an Instagram moment! A thoroughly cool Portland experience all round where even pets stay for free, great work Staypineapple!

Hotel Modera – stylish retro/modern boutique

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Situated right in the middle of the funky arts district (just two blocks from a MAX light rail station and a 6-minute walk from Portland Art Museum), the 4-star highly rated 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 this gorgeous contemporary Portland accommodation offers everything required for a refined and relaxing stay.

The boutique hotel has a zen interior courtyard complete with trendy fire pits and the city’s first-ever (very green) living wall. The sleek and chic rooms come with mod cons such as flat-screen TVs, free Wi-Fi, iPod docks and sumptuous marble bathrooms and guests receive free passes to a nearby 24-hour fitness centre. Here is also a great place to begin your exploration of Portland’s renowned foodie scene as its onsite restaurant Nel Centro offers a fine dining experience engineered by celebrated Portland chef and restaurateur, David Machado. If unique culture and funky elegance is your thing, this may be your perfect Portland hotel!

Hotel Monaco – unique eco-luxury boutique

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

The 4-star exceptionally rated 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. Located in downtown Portland (just two blocks from a MAX light rail station and a 12-minute walk from Portland Art Museum) all of the beautiful vintage styled rooms offer free WiFi, flat-screen TVs, in-room spa services as well as gorgeous fabrics and designer wallpaper. Opt for an upgraded room and you’ll be treated to living rooms, lush whirlpool tubs and wonderful city views. 

Pets are welcomed with treats, there’s a gym and 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 all-day 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 vibrant and central DownTown SouthWest…a shining example of an urban eco-hotel at its finest!

Duniway Hotel – Portland’s new lifestyle hotel

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

Billed as Portland’s newest lifestyle hotel the 4-star exceptionally rated Duniway Hotel has quickly become one of the most popular places to stay in Portland. Located on a tree-lined street in the hip and happening heart of downtown Portland – within an easy walking distance of cool shops, bars and restaurants galore – this is stylish and trendy Portland base with high standards. The sleek and polished rooms feature trendy decor and lots of mod cons, the upgraded rooms and suites are particularly spectacular. Other hotel highlights include a hip restaurant/bar run by celebrity chef Chris Cosentino, an indoor pool, a modern gym and super-lush furnished terrace that regularly hosts live music and yoga classes. Upscale Portland at it’s best!

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

The Lion and The Rose – guesthouse with bags of nostalgia

Top 12 cool and unusual hotels in Portland Global Grasshopper

Located a 10-minute walk from an Avenue MAX Station, this is no ordinary Portland guesthouse – it’s a lovingly refurbished Victorian mansion that takes guests back to a bygone era. For nostalgic souls like me, the quirky The Lion and the Rose is just perfect… it is also chic and elegant 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 seriously impressed 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 Portland gem of a place is an absolute dream! 

Hotel Deluxe – old school Hollywood glamour

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

For a film buff like me, the 4-star exceptionally rated Art-Deco 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!

Located in a central DownTown location (a 3-minute walk from Jeld-Wen Park and 10 minutes from Providence Park MAX Station) – the unique Portland hotel which dates from 1912 – is beautifully designed with soft luxurious fabrics and colours, polished wood and a 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 although with all the mod cons likeWiFi, iPod docks and flat-screen TVs. There are lots of communal spots and plenty of options to eat and drink and as a treat I enjoyed Afternoon Tea in the opulent lobby and a creative cocktail in the 1950s-style cocktail lounge. 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 $110 per night
  • To book, check prices or availability for Hotel Deluxe

The Nines Hotel – fabulous designer opulence

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

The exceptionally rated 4-star 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 characterises 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.

Located in a fabulous DownTown location the upscale trendsetting Portland hotel is located a minute’s walk away from 6th Ave MAX light rail station and 10 minutes’ walk from Portland Art Museum. The chic rooms come with flat-screen TVs and Wi-Fi and upgraded rooms offer complimentary evening cocktails. Want more? Then the library-themed cocktail bar, the modern fitness centre, the rooftop restaurant serving Asian fusion cuisine combined with sublime city views or the onsite restaurant serving up hearty American cuisines won’t disappoint. Absolute luxury all round and the service to match it. Not a budget stay but worth every penny if you want a real treat in Portland!

The Inn@Northrup Station – fun, colourful and funky

Top 12 cool and unusual hotels in Portland Global Grasshopper

This offbeat psychedelic Portland hotel will blow your socks off if you love colourful retro kitsch! The highly rated Inn@Northrup Station is situated in bustling NorthWest Portland – an Aladdin’s cave of vintage goodies, boutique shopping, 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 Aloft – the coolest airport hotel around

Top 12 cool and unusual hotels in Portland Global Grasshopper

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 the highly rated 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 if you’re searching for funky Portland airport accommodation!

Bluebird Guesthouse – cute and cosy arts & crafts home

Top 12 cool and unusual hotels in Portland Global Grasshopper

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 of Portland…within walking distance of the cool retro boutiques and cafes of Hawthorne and a short bus/car/bike trip into central 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 different and quirky Portland abode 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, just make sure you book early as rooms are taken way in advance!

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

Top 12 cool and unusual hotels in Portland Global Grasshopper

Located in a DownTown central historic building built in 1927, this is high-end landmark Portland institution of a hotel. If you want to splash out on a completely deluxe boutique experience, the 4-star exceptionally rated Heathman Hotel is where it’s at! Situated in the heart of Portland, close to all the galleries, parks and museums (and only three blocks from the Pioneer Square South MAX Station) the chic and unique Portland hotel is second-to-none for classic elegance. Although arguably its most famous accolade is being the hotel of choice for Ana and Christian’s first rendezvous in Fifty Shades of Grey!

The sophisticated boutique rooms are spacious and artfully designed and feature flat-screen TVs, French press coffeemakers, twice-daily maid service and free Wi-Fi. The truly gorgeous suites offer 4-poster beds, whirlpool tubs and living rooms. Other hotel highlights include a swish fitness centre, an intimate Tea Court Lounge offering delicious fine dining, live Jazz twice a week and complimentary wine tastings offered on weeknights. The lovely award-winning historic Portland accommodation 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 – a delightful luxury hotel option!

Society Hotel – funky and historic budget accommodation

Top 12 cool and unusual hotels in Portland Global Grasshopper

Top 12 cool and unusual hotels in Portland Global Grasshopper

This was a such a cool and characterful place. This splendid New York Style cast iron building which dates from 1881 is rich in maritime history – in its heyday it was a hotel for sailors and I can only imagine what kind of shenanigans occurred here…Nowadays the much-loved and exceptionally rated The Society Hotel is a sympathetically restored budget boutique hotel, located right in the centre of vibrant downtown Portland in the Chinatown/Old Town area filled with quirky nightlife hub, dance clubs and cocktail bars.

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, they all offer free Wi-Fi. I loved the stripped down and exposed style of the hotel’s interior which includes cool wooden floors and exposed brick walls, a gorgeous collection of historical artefacts, the trendy roof deck with views of both downtown Portland and the Willamette River and the on-site cafe which served up delicious…washed down with a craft ale in true Portland style. This hip Portland hotel is a real find if you’re a funky budget traveller!

Portland cool apartment options

Pearl Apartments – modern, swish and spacious

Top 12 cool and unusual hotels in Portland Global Grasshopper

The exceptionally rated pet-friendly 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 hip 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

Top 12 cool and unusual hotels in Portland Global Grasshopper

If you like a bit of freedom and all the creature comforts of modern living then the highly rated trendy Stay Alfred Apartments could be a good option for you. I stayed here with friends and it was pretty ideal! Located 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, it was a real treat coming from a small  UK home! It was great to stay self-catering too as Portland is chock full of foodie hangouts and it was such a pleasure to hunt out culinary delights for our evening meal. A luxurious family-friendly alternative to hotel living and thoroughly recommended.

More cool, quirky and unusual hotels in Portland

Top 12 cool and unusual hotels in Portland Global Grasshopper

  • 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 $150 per night.
  • Hotel Lucia – Set in a 1909 landmark, this chic downtown Portland hotel offers classy decor and excellent service from $130 per night.
If you liked Top 10 cool and unusual hotels in Portland we also have Top 10 cool and unusual hotels in San Francisco and Los Angeles

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.

41 Comments

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.