Portland sits near the breathtaking Oregon coast and perfectly captures the Pacific Northwest’s creative, indie spirit. When I lived here for a year, I spent time exploring its huge range of characterful accommodations, from quirky boutique hotels to sleek and modern, these are the ones that stole the show for me…
1. McMenamins Kennedy School
I was completely charmed by this unique boutique hotel, which brilliantly transformed a historic 1915 elementary school nestled in lush green gardens into a truly one-of-a-kind stay!
Inside, I found an eclectic mix of schoolhouse charm and whimsical artistic touches – I spotted vintage cloakrooms, iron candelabras, old-fashioned signs, and black-and-white class photos.
It felt bohemian and artsy in the best way – relaxed, creative, and completely unpretentious. My classroom-turned-guestroom featured vintage-style furniture, parquet floors, free WiFi, and air-con. I particularly loved how it contained a original blackboard and vintage wooden school desk!
I sipped on a ‘Ruby Ale’ at their Concordia Brewery, watched The Goonies in their private movie theater, soaked in the basement plunge pool, dined in the funky restaurant, browsed the cute gift shop, listened to a live indie band in the old gym, and explored its many themed bars – the whole place was a (vintage) vibe!
I also really enjoyed being based in the hip Alberta Arts District, I was surrounded by craft breweries, art galleries, indie shops, and lots of quirky eateries.
- To book, check prices or availability for McMenamins Kennedy School
My favorite highlights…
- Sipping on a smoky Cherry Bourbon Old Fashioned in their Honors Bar which was a cozy, quiet retreat lined with academic trophies and vintage book-filled shelves!
2. Jupiter Hotel
I found it hard not to fall for this creatively restored mid‑20th-century motor lodge! I really admired how it’s cleverly combined edgy Portland spirit with bold art, live music, and a retro-motel vibe that had been reinvented into a hip social hub!
I also watched a live rock band while sipping on craft cocktails and beer in their adjacent Doug Fir Lounge, dined on American eats in their upstairs eatery – I loved that they had plenty of vegan and gluten-free options. I also gazed at art in their 24-hour gallery and relaxed around a fire pit in their contemporary courtyard.
Funky Burnside Street was also the perfect neighborhood for me – I found myself very near indie boutiques, food trucks, live music venues, and some of the city’s coolest nightlife.
- To book, check prices or availability for Hotel Jupiter
My highlights…
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Watching elegant calligraphy tattoos come to life during Evan ESK Wilson’s seminar at the Void Tattoo Fest, hosted as part of their First Friday Artist Reception.
3. McMenamins Crystal
I discovered this hotel located in a historic red brick exterior building which dated back to 1911. Inside, I was totally won over by the eclectic and very nostalgic looking music-themed decor which featured rich wood antique-style furniture, funky artwork, hand-painted murals, cast-iron candelabras, old-fashioned signs and even colorful stained glass windows. I thought the vibe was just so unique – it felt bohemian and whimsically artistic with lots of playfulness thrown in!
The staff told me that each of the 51 rooms had been influenced by one of the standout shows at the Crystal Ballroom across the road – from Blondie to The Flaming Lips (I loved this so much)! My own guest room was music-themed and came with its signature vintage-chic style furniture, funky fringed lamps and cushions, a hand-painted head board and organic eco-friendly toiletries.
It was located in the buzzy West End part of Downtown so I very happy to be near lot of hip bars and restaurants, the famous Powell’s Books, the Pearl District, and the lively Jimmy Mak’s Jazz Club.
I watched live music and a funny comedy show at the Crystal Ballroom, drank craft beer and hand-mixed cocktails at the themed bars, checked out the two on-site restaurants which served up Northwest cuisine, took a dip in the illuminated basement saltwater soaking pool and checked out the onsite art gallery which was music-themed, of course!
- To book, check prices or availability for McMenamins Crystal Hotel
My favorite highlights…
- Dining on hazelnut-topped butternut squash ravioli washed down with a potent Three Rocks Spiced Rum in their eclectically-decorated onsite Hal’s Café!
4. Sentinel Hotel
I was genuinely impressed by this 5-star historic boutique hotel in downtown. It stood out to me because of its blend of elegant historic architecture and creative, locally inspired design.
I was in awe of the early‑20th‑century Renaissance‑style architecture and the superb vintage modern decor which included a grand staircase, jade‑green walls, luxurious tweed and wood furnishings, high ceilings complete with impressive chandeliers, black and white prints of intellects, worn leather sofas, mahogany paneling, 20th-century local art, and lots of books!
It felt sophisticated and luxurious but not so much it felt intimidating, I still felt very welcomed! My guest room was equally as impressive and had boutique-style style decor with plush pillow-top bed dressed in Frette Italian linens, a pet-friendly policy, a well-stocked minibar, a flat-screen TV, and my favorite feature – a cute pillow and speaker menu! I opted for the plush hypoallergenic and the Tivoli Bluetooth Clock Radio!
It was also ideally placed for everything – it was i central downtown near a streetcar stop and within walking distance of Powell’s Bookstore, the Portland Art Museum and buzzing restaurants and nightlife.
I also loved the secret hidden wood-paneled library, the daily organic breakfast which came with lots of veggie options, the modern fitness center, the on-site Starbucks cafe, the classic American fare at Jake’s Grill and the craft-cocktails at the stylish Jackknife Bar.
My favorite highlights…
- I loved the awesome Well & Fit kit in my guest room which came with a handy yoga mat, skipping rope, and even a tablet which came pre-loaded with fun fitness videos!
- Dining on the fragrant honey at breakfast which was produced by the bees living in the beehives on the hotel rooftop, I thought this was such a cute touch!
- To book, check prices or availability for Sentinel Hotel
5. Moxy Downtown
I found this place located in a sleek black high-rise building adorned with pink neon lights. Inside I discovered a tech-savy and trendy industrial-chic world with modular seating, lashings of concrete and metals and and quirky details such as vintage cameras, bicycles mounted on walls, vinyl record players and graffiti-style murals.
To me, it felt like a cool urban retreat with a playful and fun vibe and a youthful buzzy energy. My guest room that featured a light, contemporary design, wooden floors, a large comfortable bed, retro-chic furniture, modern art prints and funky slogan cushions.
I thought its central downtown location was superb and I found myself right on the doorstep of awesome local nightlife, excellent shopping, dining, and lots of cultural attractions.
I also made full use out of their four onsite restaurants which gave me a choice of sushi to classic American dishes, the sociable bar and communal hang out areas, and the 24/7 modern fitness center.
- To book, check prices or availability for Moxy Downtown
My personal highlights…
- Drinking a lone birch chardonnay accompanied by lots of truffle popcorn while chatting to other guests in the funky onsite bar.
6. Hotel Vintage
I found a classic, early 20th-century brick facade with large, arched windows and inside I found a huge, striking lobby with a long spiral staircase, art sculptures, colorful slogan pillows, and chandeliers shaped like bunches of grapes!
I stayed in a loft-style guest room with a flat-screen cable TV, a mini-fridge, plush bathrobes, city views, and a handy yoga mat!
I discovered it in downtown Southwest, near Providence Park and the Pearl District. It was an 11-minute walk from the Portland Art Museum. The hotel was also at the center of a lot of entertainment action.
The Pazzo restaurant served up a buffet breakfast, local wines, and Italian cuisine. The Bacchus Bar, located on-site, served craft beers and wines, and I loved the fun old-school arcade games and the pool table.
I also found a modern 24-hour fitness center, a pet-friendly policy (and a few cute pooches!), a fine restaurant serving up a mix of global and American cuisine and sociable wine tasting sessions in its lounge room bar.
- To book, check prices or availability for Hotel Vintage
My highlights…
- I loved their elevated versions of classic breakfast dishes – I opted for the Farmhouse Hash which came with red potatoes, spinach, cherry tomatoes and the unique addition of brussels sprouts!
7. Duniway Hotel
Billed as the city’s newest lifestyle hotel, I thought the overall design was stylish and trendy with an upscale feel. I saw chic contemporary furniture, exotic rugs, lashings green plants, and art prints adorning the walls.
I stayed in a spacious guest room with featured modern boutique style decor, free WiFi, high-thread-count linens, a visual doorbell, fine city views, and an espresso machine.
It was located in the Central Business District so I was within walking distance of independent shops, bars, and restaurants. The Portland Art Museum, the Arlene Schnitzer Concert Hall, and MAX Light Rail were nearby.
It also featured an onsite restaurant overseen by celebrity chef Chris Cosentino, an onsite eatery and bar, an indoor swimming pool, a modern gym, and a furnished terrace that regularly hosted live music and yoga classes (which I loved)!
- To book, check prices or availability for Duniway Hotel
My personal highlights…
- Relaxing in the Mayrose bar with a Scotch-based Raspberry Lynchburg cocktail and truffle fries at happy hour.
8. Ace Hotel
I was a big fan of this funky mid-range accommodation option that doubled as a local hipster hangout. It was housed in a historic building in the funky West End neighborhood which was filled with great nightlife, vibey bars, excellent restaurants, and fabulous independent boutiques.
The overall look was very hip and creative, with dark wood and colorful retro-styled furniture. There was a funky communal vibe about the place and I easily got casually chatting with quite a few guests.
My guest room, which was decorated by local artists, had dark wooden floors, an exposed brick wall accent wall, and quirky features such as a vinyl record player. Some rooms have shared bathrooms, but all came with free WiFi, minibars, and flat-screen TVs.
I dined on home-cooked locally sourced food, a continental breakfast, and a vast range of alcoholic drinks in the cozy Clyde Common restaurant and bar overseen by Chef Carlo Lamagna, who offered a diverse range of innovative menu choices.
Other stand out features included the bespoke handmade motorcycle which was created for the hotel by artist Jordon Hufnagel and the lobby bar where I played a vinyl record and messed around in the vintage photo booth.
- To book, check prices or availability for The Ace Hotel
My personal highlights…
- Discovering the classy Pacific Standard bar which was just around the corner and set up by famous bartender Jeffrey Morgenthaler – I loved the dark wood book shelves and their coffee cocktails, especially their Expresso Martinis!
9. Jupiter Next
This is the new sister hotel of the Jupiter Hotel, but I found it was an officially higher-graded hotel. It had been designed by trendy Works Progress Architecture, and the hotel had fine views of the city and the West Hills. The design was trendy industrial-chic, with a concrete-and-steel staircase (a design piece by Laura Sol), a concrete fire pit, and lots of black and glass.
My room had a city-inspired headboard, large windows, modern art, a glass bathroom, a signature knit throw from Seek & Swoon, a voice-activated in-room concierge, high-speed Wi-Fi, and a large flat-screen TV.
It was located on Eastside Burnside Street so I found lots of independent boutiques and live music venues on my doorstep, near Voodoo Donuts and Revolution Hall.
The hotel also had space to work, relax, and socialize and I was especially fond of the tropical-themed onsite restaurant and bar which served American cuisine, a tasty buffet breakfast, and handcrafted cocktails and even turned into a disco in the evenings. There was also an open-air lounge on the fifth floor which had awesome city views.
- To book, check prices or availability for Jupiter Next
My personal highlights…
- I really liked the little details especially the “Local Hookups” key-card program which had awesome discounts for local attractions and restaurants the neighborhood and the fun digital concierge device which was named Roxy!
10. Hoxton Hotel
I found this boutique hotel housed in a restored 1906 building, and inside it featured modernist furniture, quirky ornaments, a pastel color scheme, and large windows that flooded the place with natural light.
Guest rooms ranged in size from small to spacious, and my room featured dark woods, art, a flat-screen TV, free WiFi, air conditioning, tall windows offering city views, and black-tiled private bathrooms.
It was located in the city’s historic Chinatown, so I was within walking distance of great restaurants, interesting shops, and a MAX Light Rail station. I also found that the famous White Stag sign and Tom McCall Waterfront Park were nearby.
I also really liked their rooftop restaurant that combined American food with incredible city views, a coffee shop that served up offers pastries and coffee, and a speakeasy-style basement bar. I spent a lot of my time in the trendy rooftop bar which served up creative themed cocktails inspired by the local area, craft beers, and snacks.
- To book, check prices or availability for The Hoxton Hotel
My highlights…
- The high-end and exclusive design details – I found out from staff that my room was decorated with ceramics by Clay Factor and the artwork was selected by the local gallery Upfor,
11. Hotel Zags
I thought this design boutique reflected the city’s unique spirit. I personally thought it was a very striking place with retro-modern furniture, contemporary art, and lashings of wood and greenery.
My guest room featured a flat-screen cable TV, air conditioning, free Wi-Fi, an iPod dock, and a chic-looking marble bathroom. I also received a complimentary pass to a nearby 24-hour fitness center.
I found it situated along Willamette River in the downtown arts district, just two blocks from a MAX light rail station and a 6-minute walk from the Portland Art Museum. I was also near the Farmer’s Market, South Waterfront Park, and the Hawthorne Asylum Food Cart Pod.
Other amenities I discovered were the stylish interior courtyard which came with trendy fire pits, the city’s first-ever living green wall (which was spectacular!), a 24-hour store, a tasty buffet breakfast, and an onsite restaurant, Nel Centro, which served up a fine dining experience engineered by the highly-regarded local chef and restaurateur David Machado.
- To book, check prices or availability for Hotel Zags
My favorite highlights…
- I loved their awesome Gear Shed where I could borrow everything from bicycles and skateboards (complete with pads and helmets) to longboards, cameras, and hiking boots!
12. The Heathman
I found this famous place housed in a downtown historic building from 1927, it offered a premium boutique lodging and had a very upscale and romantic vibe – it even had been mentioned in the Fifty Shades of Grey novels!.
I really like that it had both a traditional charm combined with contemporary amenities. My room was well-appointe and spacious with a chic design, a French press coffee maker, luxurious linens and complimentary Wi-Fi. The reception staff showed me a typical suite and that included a lush four-poster bed, a hot-tub, and a separate living space.
I found myself conveniently close to popular cultural attractions in the city, including galleries, parks, and museums and it was just a short walk from the Pioneer Square South MAX Station.
The hotel’s facilities included a state-of-the-art fitness center and the Tea Court Lounge which served up fine gourmet food. I especially loved the cultural events though and I saw a live Jazz music session and went to a wine tasting evening too!
- To book, check prices or availability for The Heathman Hotel
My personal highlights…
- Meeting fellow guests while sipping on Oregon-produced Pinot Noir at the evening wine hour which was held in their onsite chic bar.
13. Hotel Deluxe
This was an upscale Art-Deco hotel that paid homage to the cinematic arts! Inside I found the place adorned with a fine collection of photographs from classic films ranging from the 1930s to the 1960s, with different floors dedicated to iconic directors and actors!
I found it to be a pop-up cinema, where I enjoyed classic films along with a selection of craft beers and cocktails. It was centrally located downtown, just a short walk from Jeld-Wen Park and Providence Park MAX Station. It is a historic structure originally built in 1912. Its design incorporates soft textiles, polished woods, and a palette that reflects classic sophistication.
I really enjoyed having Afternoon Tea in the grand lobby and enjoying a hand-crafted in the lounge which reminded me of a 1950s cocktail bar!
- To book, check prices or availability for Hotel Deluxe
My personal highlights…
- I loved how each floor was dedicated to different golden age film star – I stayed on the Rita Hayworth floor which was adorned with her film stills and photographs.
14. Hotel Eastlund
I really liked this boutique hotel which had a striking 1960s-inspired design. It combined geometric elements with a 1960s aesthetic palette, creating a sophisticated and awesome vibe.
My room had complimentary Wi-Fi, a flat-screen TV, and gorgeous city views and my favourite feature – a soaking tub!
It was situated on the east side of the city, so I was conveniently located 1.5 miles from Pioneer Courthouse Square and 3 miles from the Japanese Garden.
I also really liked the cute little artisan bakery, the upscale wine bar, the handy convenience shop, the modern fitness center, and the trendy rooftop restaurant with fine city views and a menu filled with cocktails and craft beer.
- To book, check prices or availability for the Eastlund Hotel
My personal highlights…
- The vegan eclairs and chai lattes served at the cute onsite bakery Citizen Baker, on healthier days I opted for raspberry kombucha.
15. The Nines Hotel
Here I found a upscale design haven with a gorgeous blend of art deco elegance and a vast collection of contemporary art. I really liked that it paid tribute to the building’s original purpose when it was built in 1909 as the Meier & Frank flagship department store and headquarters.
I loved how it featured a combination of artistic contributions from the local art college and some cool amenities including a library-themed cocktail bar, a stylish fitness center, a trendy rooftop restaurant which served up Asian fusion dishes with panoramic city views, and a more casual restaurant that specialized in American cuisine.
My room was equipped with a flat-screen TV and complimentary Wi-Fi, my favorite feature – complimentary evening cocktails!
Located in the center of downtown, I was conveniently located so I was just a minute from the 6th Ave MAX light rail station and a ten-minute walk from the Art Museum.
- To book, check prices or availability for Hotel Nines
My highlights…
- Dining on sweet potato miso ramen and mulled sake while gazing at Mount Hood in their trendy rooftop Asian restaurant The Departure Lounge.
Wow these are some seriously unique hotels, I think my favorites are number 4 and number 6 – just wow!
It is vacation time soon! Portland sounds like a great destination, thanks for all the information and tips on these hotels!
I am also looking for visiting Portland in next few months and this blog is really helpful for me for having a best hotel for stay. Thanks for sharing this blog with us 🙂
Hey, this is awesome! Once COVID is gone I will definitely rush and go to Ace Hotel it’s super cool, simple, and there’s a vintage vibe on it, plus I want to try renting a bike while exploring the streets nearby. Thank you for sharing this.
Thank you so much to share such a beautiful place. I had no idea Ana and Cristian´s first rendezvous was filmed at The Heathman Hotel! I especially love Duniway and Modera! I can not think about them in my own think
Portland is on our list as soon as Covid-19 dies down!
I stayed at the Sentinel last year, so glad to see it make this article! I had a great time there, the room was fantastic, staff very helpful and the location was excellent. Great article, makes me want to get back to Portland even more now.
The Caravan Tiny House hotel is more like my thing. My mom and I watch this show called Tiny House Hunting and are fascinated by the fantastic use of such little space to fit in every requirement. I’d love to stay at a property like that because I certainly see myself adopting the Tiny House Living lifestyle later in life.
These places are so cool and beautiful! Love your photos!!
Sentinel hotel with all those books! I’d probably never leave
Awesome pics!! I’ve never thought that exploring Hotels would be fun and heart-melting. I just loved them, each and every hotel is having its own elegance.
Great collection.In love with the charming looks of these hotels.Will book any of them if I have to go Portland in future.
hi Beth Pinches,
So nice post just wow. Every hotel attracting me so much. Stunning designs,great thoughts and comfort all are getting together who needs more.Since I am a fan of retro style fall in love with the “Hotel Eastlund”.Its interior design amazed me.
Thank you
Great list of hotels that you have provided one of them is my favourite name Duniway Hotel I was thinking to know about this one but by chance have read about it on your site really thanks a lot sir
Really a beautiful blog with so much information about these amazing hotels. Thanks for sharing!
Jupiter Hotel seems like my kind of place! But every suggestion is amazing.
Hotel Vintage really made an impression. I love the rustic style incorporated into modern world. I guess the price is fair.
So many beautiful hotels!!! I had no idea Ana and Cristian´s first rendezvous was filmed at The Heathman Hotel! I especially love Duniway and Modera!
Love the Ace Hotel. Just that we probably won’t be checking in solo. It looks cool but pretty spooky too .
These hotels are real gems. I am charmed by the McMenamins Crystal hotel.
Photos are so amazing the hotels looks so gorgeous.
Hi, Beth Pinches I like the hotel pearl, thanks for sharing!
Wow awesome collection of hotels in Portland!
NIIICEEE! Love Portland – everyone should visit at least once in their lifetime!
Very cool list, I like that painting in Hotel Modera!
Your site is Perfect!!!!! Amazing!!!
Staypineapple looks ace! Awesome list Beth – lots of variety! 🙂
Loved your post! Cool Photos!!
This is first time I am visiting your website and I find this post very very useful thanks for giving such a great information..
Keep up the good work…I will love to visit your site again and again….
Hotel Modera is the exquisite one! Wish to stay there one day!
I like hotel vintage the best! But hotel deluxe really looks fancy, would love to take photos there!
Very detailed with lots of cool tips and inspiring pictures. I love it!
All hotels seem good for stay. I am planning to visit Portland this Christmas, which one would you recommend for stay?
We stayed at the Heathman last year and loved it, but there are some other great looking hotels on the list that we have to try out on our next visit!
Portland is the best because of it’s mindset, “keep Portland weird”! I love how unique it is. Oh, and don’t forget about VooDoo Donuts! (I also love the Ace Hotel!)
-Gabby
Hotel #3 liked the most of all. Thank you for amazing post 🙂
Wow, really great list of hotels!
SUCH funky hotels, I like the look of Jupiter, really ever so unique!
Laura xo
Gorgeous! I’m a sucker for a quirky hotel. Hopefully I’ll get to visit Portland one day soon.
These hotels are so stunning, Beth! I will definitely stay in some of them when I visit Portland!
Bookmarking this list for my trip to Portland. Looking forward to it!
Portland is amazing!
Great list and I love that cat on the wall in Ace Hotel
Great list of hotels in Portland – like the look of the Ace Hotel.
Great list with amazing looking hotels!! They all look so cool! – C.
I love finding these fun and cool spots in every city!
How do you find these gems?
This is such a cool list of interesting hotels! I still need to visit Portland, and will take this list with me when I go 🙂
Sorry to miss it Aaron! so many amazing quirky hotels to choose from, we’ll have to do a list take #2!
Thanks for sharing the link Scott!
Fabulous looking place and hotels! Very cool indeed 😉
Emma, you would love it I am certain!
Want a romantic place with hot tub under 100$ suggestions?
You might struggle with that one Valerie, although I bet you’d find some last minute deals if your time is flexible!
Love love love this! Portland is such a cool city! I always love visiting because there’s so many cool hip things to do or see. And you nailed it adding the Jupiter. That place is so cool! Keep rocking it.
Portland is so close to us in Vancouver, we really should visit! We hear the craft brewery scene is great. And what a cool selection of funky boutique hotels we have to choose from too! Think we’d like the Hotel Monaco very much :-).
Sand in my suitcase you should really take advantage of that, such a brilliant city, craft brewerys everywhere!
I’d heard that Portland was a hipster’s paradise and the hotels certainly confirm that. McMenamins Kennedy School would be my hotel of choice, it looks so quirky
Doesn’t it look fab suze? I can’t wait to go back to Portland one day!!!
These are all so cool! I think my favorites would be either the Ace or the Vintage. Hopefully visiting Portland soon, so I will have to refer back to this list! Thanks for sharing!! 🙂
I have never been to Portland, but if you asked me to stay in one of these hotels I would definitely choose McMenamins Kennedy School – boutique kitsch. It’s so odd, indeed. I can already imagine myself there. Such a cool place.
Love Portland and love the look of these hotels! Especially The Ace – looks very cool!
I know JB, such a cool city… a testament to what is possible when the right kind of proactive, creative people put their heads together!
Those hotels look amazing and I wish I had known about them before I went to Oregon. Thank you for sharing and they absolutely look amazing and inviting. I really like the retro look of the Jupiter Hotel.
Don’t they look fab? I definitely want to try a couple of them out on my next trip!!