I lived in Portland, Oregon for a year, and during that time, I spent many weekends exploring the huge range of accommodations around the city. I found many characterful places to stay. Some were quirky, some were sleek, and some were very modern. Every one of them felt full of creative energy and indie spirit, which is what makes the Pacific Northwest feel so alive.
Some of my favorites were smaller boutique hotels with a quirky charm, while others had that cool, sleek look. The coast is not far from Portland, and even in the city, the vibe reminded me of it—peaceful, fresh, and different. I stayed in places that felt modern, some that were characterful, and others that mixed both. The creative feel was strong in each place I picked. The people, the design, the vibe—each hotel offered something unique.
From what I have explored, this city has more than just hotels—it offers an experience. Whether it’s a boutique place with a local touch or a more modern spot with a sleek design, Portland gives you all. And with its deep indie roots and Pacific Northwest style, it always brings a fresh, creative twist.
McMenamins Kennedy School
I once lived in Portland, Oregon for almost a year. During that time, I went on a mission — exploring the most quirky, characterful places to stay. One of my all-time favorites was the McMenamins Kennedy School, a unique, historic boutique hotel set inside a former 1915 elementary school. Yes — a real school, now beautifully transformed into one of the most unforgettable accommodations in the Pacific Northwest.
This place had charm like no other. The old schoolhouse still had its cloakrooms, real blackboards, and wooden desks. I spotted vintage touches everywhere — from iron candelabras, old-fashioned signs, and black-and-white class photos to whimsical art and eclectic colors. The vibe felt bohemian, relaxed, and perfectly unpretentious. My classroom-turned-guestroom came with warm vintage-style furniture, smooth parquet floors, comfy air through air-con, and free WiFi.
In the evening, I sipped a cold Ruby Ale brewed right at the Concordia Brewery. Later, I watched The Goonies in their private movie theater, soaked in the warm basement plunge pool, and dined in their funky restaurant. After dinner, I browsed the cute gift shop, listened to a live indie band in the old gym, and explored their many themed bars. The whole vibe felt cool, weird, fun — completely artistic and very Portland.
I was based right in the Alberta Arts District, a hip area surrounded by craft breweries, creative eateries, indie shops, and local art galleries. It was the perfect spot to feel the city’s indie, creative spirit near the coast — pure Pacific Northwest energy.
One night, I was in their cozy, quiet Honors Bar — a true retreat filled with academic trophies, vintage items, and book-filled shelves. I was sipping a smoky Cherry Bourbon Old Fashioned, and I thought… this really is a one-of-a-kind experience.
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My favorite highlights…
• Drinking fresh Ruby Ale at the Concordia Brewery
• Floating in the warm basement plunge pool after a film night
• Catching a live indie band while surrounded by vintage school vibes
• Getting lost in a room filled with vintage, artsy, and creative energy
Jupiter Hotel
The Jupiter Hotel is one of the most funky and edgy spots I’ve ever stayed in Portland. A creatively restored mid 20th-century motor lodge, this retro-motel turned social hub truly stands out. The hotel has bold personality and spirit, with pop-art murals, retro-modern decor, and industrial-chic touches that feel both artsy and alive.
My Headliner King Room was decorated in blue and white, filled with eco-friendly amenities, a large flat-screen TV, fast Wi-Fi, and a fun chalkboard where I actually chalked my own message. It felt modern but playful. I could hear live music coming from the Doug Fir Lounge, where I later sipped on craft cocktails and beer, while a rock band played on stage.
I also dined on great American eats in their upstairs eatery, with lots of vegan and gluten-free options available. I gazed at their gallery, open 24-hour, and relaxed near the fire pit in the contemporary courtyard. The whole vibe was chill and full of good energy.
Located right off Funky Burnside Street, the neighborhood had an indie charm — filled with cool boutiques, colorful food trucks, exciting venues, and lively nightlife. Truly one of the coolest parts of the city to stay in.
What I really loved was being part of the Void Tattoo Fest, where I watched elegant calligraphy tattoos created live by Evan ESK Wilson during a special seminar hosted at the First Friday Artist Reception. It was exciting to be a part of something so creative.
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My favorite highlights…
• Playing with the chalkboard in my room and writing a fun message
• Late-night music and cocktails at Doug Fir Lounge
• Hanging out in the courtyard under the stars with a fire glowing
• Watching live tattoos at the artist reception and chatting with real creatives
McMenamins Crystal
I recently stayed at the McMenamins Crystal Hotel, and it felt like stepping into a world of funky charm and artistic magic. I had seen a photo of the historic red brick building, dated 1911, and I was curious. When I finally discovered it downtown, I was immediately won over. Inside, the decor was music-themed, totally nostalgic, and full of playfulness. The eclectic mix of rich wood, antique-style furniture, funky artwork, hand-painted murals, cast-iron candelabras, and colorful stained glass windows gave it a unique and bohemian vibe.
Each of the 51 rooms had a connection to standout shows at the Crystal Ballroom, just across the road — like Blondie and The Flaming Lips. My guest room had a signature vintage-chic style with fringed lamps, soft cushions, a hand-painted head board, and organic, eco-friendly toiletries. It felt warm and creative.
The staff were kind, and the location was buzzy in the West End of Downtown. I felt happy being so near great bars, local restaurants, Powell’s Books, the Pearl District, and the lively Jimmy Mak’s Jazz Club — all so famous for their energy.
One night, I watched live music and a funny comedy show at the Crystal Ballroom, then drank craft beer and hand-mixed cocktails at the themed bars. I also checked out two on-site restaurants serving tasty Northwest cuisine. Later, I took a dip in the glowing illuminated basement saltwater soaking pool and wandered through the art gallery, which stayed true to the hotel’s music-themed soul.
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My favorite highlights…
• Late-night dining at Hal’s Café, a colorful, eclectically-decorated spot
• The creamy hazelnut-topped butternut squash ravioli, perfectly washed down with a potent Three Rocks Spiced Rum
• Exploring every funky corner of the hotel — this area truly inspires
Sentinel Hotel
The Sentinel Hotel is a true 5-star boutique hotel in downtown Portland. The architecture is historic and elegant, with early 20th century Renaissance style touches that feel both grand and timeless. When I first walked in, I was amazed by the grand staircase, the soft jade green walls, high ceilings, and impressive chandeliers. The decor mixes vintage modern charm with local art, black and white prints of great intellects, and worn leather sofas that rest against mahogany paneling. It felt very sophisticated, but never intimidating—I felt truly welcomed.
My guest room had a boutique-style layout with a plush pillow-top bed dressed in soft Frette Italian linens, a well-stocked minibar, a flat-screen TV, a cute pillow, and even a speaker menu. I loved the hypoallergenic bed setup and the Tivoli Bluetooth Clock Radio. They also provided an awesome Well & Fit kit that came with a handy yoga mat, a skipping rope, a tablet pre-loaded with fun fitness videos, and other thoughtful extras.
The hotel is ideally placed—central, near a streetcar stop, and within walking distance of Powell’s Bookstore, the Portland Art Museum, buzzing restaurants, and exciting nightlife. My mornings began with a daily organic breakfast that included veggie options and fragrant honey made by bees from rooftop beehives—a truly cute touch.
For food, I enjoyed classic American fare at Jake’s Grill, craft-cocktails at the stylish Jackknife Bar, and coffee from the on-site Starbucks cafe. There was also a modern fitness center for guests.
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My favorite highlights…
• Reading in the secret, hidden, wood-paneled library
• Waking up to fresh organic breakfast with fragrant honey from the rooftop
• Trying out the full Well & Fit kit and watching fitness videos in-room
Moxy Downtown
The Moxy Downtown is the kind of place that instantly grabs your attention. A sleek, black high-rise building with glowing pink neon lights, it gives off a strong urban retreat vibe. The inside is tech-savvy, trendy, and full of industrial-chic style. You’ll find modular seating, raw concrete, shiny metals, and quirky details like vintage cameras, bicycles mounted on walls, vinyl record players, and bold graffiti-style murals.
My guest room had a light, contemporary design, smooth wooden floors, a large comfortable bed, cool retro-chic furniture, modern art prints, and funky slogan cushions that gave it extra life. Everything felt cool, fun, and full of youthful, buzzy energy.
The central downtown location was superb. Right at my doorstep were local nightlife, excellent shopping, creative dining, and some of the city’s best cultural attractions.
There were four onsite restaurants to choose from. I tried both sushi and some solid classic American dishes. I also spent time in the sociable bar and the communal hang out areas, then worked out in the 24/7 modern fitness center.
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My personal highlights…
• Drinking a lone birch chardonnay with truffle popcorn
• Chatting with other guests in the funky onsite bar
• Taking in the design — from the vinyl record players to the mounted bikes
Hotel Vintage
Hotel Vintage brings a classic vibe with its early 20th-century style and brick facade. The large, arched windows pull in light that fills the huge, striking lobby. A long spiral staircase, bold art sculptures, colorful slogan pillows, and chandeliers shaped like bunches of grapes create a fun and stylish mood.
I stayed in a loft-style guest room with a flat-screen cable TV, a cool mini-fridge, and soft plush bathrobes. I loved the open city views, and the yoga mat was a nice touch for stretching before bed. The hotel is in downtown Southwest, close to Providence Park, the Pearl District, and only an 11-minute walk to the Portland Art Museum. It sits in the center of all the entertainment action.
Food was amazing. I tried the Pazzo restaurant for buffet breakfast and Italian cuisine, paired with great local wines. At night, I visited the Bacchus Bar, located on-site, and enjoyed craft beers, more wines, and some old-school arcade games and a pool table.
There was a modern, 24-hour fitness center, and I loved the pet-friendly policy — I even met some friendly pooches in the lobby. The hotel also had a fine restaurant with global cuisine and American cuisine, plus sociable wine tasting sessions in the cozy lounge room bar.
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My highlights…
• Tasting elevated versions of classic breakfast dishes
• Enjoying the Farmhouse Hash with red potatoes, spinach, cherry tomatoes, and crispy brussels sprouts
• Hanging out in the lounge room bar after an arcade match
Duniway Hotel
The Duniway Hotel is the city’s newest lifestyle hotel, and I instantly thought its overall design had a stylish, trendy, and upscale feel. The lobby had chic contemporary furniture, exotic rugs, and lashings of green plants and art prints adorning the walls.
I stayed in a spacious guest room that featured modern, boutique style decor, free WiFi, soft high-thread-count linens, a visual doorbell, fine city views, and a sleek espresso machine. It was located in the Central Business District, within walking distance of independent shops, local bars, great restaurants, the Portland Art Museum, and the Arlene Schnitzer Concert Hall. The MAX Light Rail was also nearby, which made getting around the city easy.
The hotel also featured an onsite restaurant overseen by celebrity chef Chris Cosentino, plus an onsite eatery and bar. I spent a few hours at the indoor swimming pool, got a workout in the modern gym, and enjoyed the furnished terrace that regularly hosted live music and fun yoga classes — I truly loved the whole vibe.
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My personal highlights…
• Relaxing at the Mayrose bar during happy hour
• Sipping a Scotch-based Raspberry Lynchburg cocktail with crisp truffle fries
• Listening to live music while stretching on the terrace during early yoga classes
Ace Hotel
The Ace Hotel is a funky, mid-range accommodation that feels more like a local hipster hangout than a regular place to sleep. It’s in a historic building right in the heart of the West End neighborhood, surrounded by lively nightlife, vibey bars, excellent restaurants, and independent boutiques. Everything about this hip, creative hotel stood out to me.
My guest room was decorated by local artists with dark wooden floors, an exposed brick wall, and a cool accent wall. There were quirky features like a vinyl record player that I actually played, and though some rooms had shared bathrooms, mine came with free WiFi, cold minibars, and crisp flat-screen TVs.
I dined on home-cooked, locally sourced food, enjoyed a simple continental breakfast, and had a few alcoholic drinks in the cozy Clyde Common restaurant and bar, led by Chef Carlo Lamagna, who offered a diverse, innovative menu choices.
The lobby bar had stand out features too, including a bespoke, handmade motorcycle made by artist Jordon Hufnagel. I had fun in the vintage photo booth, where I snapped some keepsakes.
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My personal highlights…
• Discovering the classy Pacific Standard bar just around the corner
• Chatting with a famous bartender — Jeffrey Morgenthaler
• Trying strong coffee cocktails and smooth Expresso Martinis near tall book shelves and warm dark wood
Jupiter Next
Jupiter Next is the sister hotel to the original Jupiter Hotel, but it’s officially more higher-graded and polished. The building was designed by Works Progress Architecture, with a look that’s very trendy and industrial-chic. You’ll spot bold choices like a concrete-and-steel staircase designed as a design piece by Laura Sol, along with a glowing concrete fire pit, plenty of black, and reflective glass touches.
My room was a perfect balance of comfort and art. It had a city-inspired headboard, large windows, modern art, and a clean glass bathroom. The bed came with a signature knit throw from Seek & Swoon, and the tech stood out: a voice-activated in-room concierge, high-speed Wi-Fi, and a large flat-screen TV made everything easy.
The location on Eastside Burnside Street meant I had independent boutiques, live music venues, Voodoo Donuts, and Revolution Hall right at my doorstep. I had space to work, relax, and socialize, and I loved the tropical-themed onsite restaurant and bar. I enjoyed some American cuisine, a tasty buffet breakfast, and fresh handcrafted cocktails that later matched the fun disco energy during the evenings. Up on the fifth floor, the open-air lounge gave me awesome city views.
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My personal highlights…
• Noticing the little details like the Local Hookups key-card program that gave awesome discounts to local attractions and restaurants in the neighborhood
• Using the digital concierge device named Roxy to discover cool hidden gems
Hoxton Hotel
The Hoxton Hotel is a boutique hotel set inside a restored 1906 building, blending charm with fresh design. Inside, you’ll see modernist furniture, quirky ornaments, and a soft pastel color scheme. The large windows fill the space with natural light, giving the place an open and inviting mood.
Guest rooms come in all sizes — from small to spacious. My room had deep dark woods, curated art, a flat-screen TV, free WiFi, and cool air conditioning. I loved the tall windows with city views and the sleek black-tiled private bathrooms.
The hotel is located in historic Chinatown, within walking distance of great restaurants, interesting shops, and the MAX Light Rail station. I also found the famous White Stag sign and Tom McCall Waterfront Park nearby, which made exploring super easy.
The hotel features a rooftop restaurant serving tasty American food with incredible city views. I often stopped at the coffee shop for pastries and coffee, or headed down to the speakeasy-style basement bar. My favorite spot though was the trendy rooftop bar, known for creative themed cocktails inspired by the local area, craft beers, and savory snacks.
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My highlights…
• Seeing high-end, exclusive design details in every space
• Learning from the staff that my room was decorated with ceramics by Clay Factor
• Viewing artwork selected by the local gallery Upfor right in my room
Hotel Zags
Hotel Zags is a design boutique that reflects the city’s unique spirit. The space feels striking, filled with retro-modern furniture, bold contemporary art, warm wood, and plenty of fresh greenery.
My guest room had a flat-screen cable TV, cool air conditioning, free Wi-Fi, an iPod dock, and a chic-looking marble bathroom. They even gave me a complimentary pass to a nearby 24-hour fitness center, which was a great bonus. The hotel is situated near the Willamette River, right in the downtown arts district, just two blocks from the MAX light rail station and a quick 6-minute walk to the Portland Art Museum. I also explored the Farmer’s Market, South Waterfront Park, and the Hawthorne Asylum Food Cart Pod — all close by.
The amenities at Zags were smart and fun. I loved the stylish interior courtyard, especially the trendy fire pits. I was amazed by the living green wall, something I had never seen before. There’s also a 24-hour store, a tasty buffet breakfast, and an onsite restaurant called Nel Centro, a fine dining experience engineered by highly-regarded local chef, restaurateur David Machado.
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My favorite highlights…
• The awesome Gear Shed, where I could borrow fun things like bicycles, skateboards, safety pads, helmets, and even longboards, cameras, and hiking boots
The Heathman
The Heathman Hotel is a famous gem in downtown Portland. Housed in a historic building from 1927, it offers premium boutique lodging with an upscale, romantic vibe. It was even mentioned in the Fifty Shades of Grey novels, which adds a fun bit of fame to its story.
The rooms bring traditional charm with contemporary amenities. My room was well-appointed, very spacious, and had a chic design. I enjoyed the French press coffee maker, the soft luxurious linens, and complimentary Wi-Fi. One of the reception staff even showed me a typical suite with a lush four-poster bed, a relaxing hot-tub, and a separate living space.
It’s conveniently close to many popular cultural attractions in the city—I took a short walk to visit galleries, beautiful parks, and local museums. It’s also near the Pioneer Square South MAX Station, so it’s easy to get around.
The hotel’s facilities include a state-of-the-art fitness center and the lovely Tea Court Lounge, where I had some truly fine gourmet food. There were also cultural events during my visit — I enjoyed a live Jazz music session and attended a wine tasting evening, both hosted onsite.
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My personal highlights…
• Meeting other travelers and fellow guests
• Sipping Oregon-produced Pinot Noir during the relaxed evening wine hour in their chic bar
Hotel Deluxe
Hotel Deluxe is an upscale, Art-Deco hotel that feels like a warm homage to the cinematic arts. The walls are adorned with a fine collection of photographs from classic films of the 1930s through the 1960s, and different floors celebrate iconic directors and iconic actors. I stayed on the Rita Hayworth floor, which was filled with her film stills and beautiful photographs — a true nod to a golden age film star.
There was even a pop-up cinema where I enjoyed a curated selection of movies with fresh craft beers and smooth cocktails. The hotel is centrally located in downtown, just a short walk from Jeld-Wen Park and the Providence Park MAX Station.
This historic structure, built in 1912, has a unique design filled with soft textiles, glossy polished woods, and a rich palette that creates a feel of classic sophistication. One afternoon, I had Afternoon Tea in the grand lobby, followed by a hand-crafted drink in the lounge, which felt like a true 1950s cocktail bar.
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My personal highlights…
• Immersing myself in a golden age vibe while walking each themed floor
• Sipping cocktails under the glow of film stills from the 1930s
• Sitting in the lounge, imagining the scenes from old classic films
Hotel Eastlund
Hotel Eastlund is a boutique hotel with a striking look and a cool 1960s-inspired design. The space mixes bold geometric elements with a soft 1960s aesthetic palette, giving off a sophisticated, awesome vibe from the moment you step inside.
My room had everything I needed — complimentary Wi-Fi, a clear flat-screen TV, and gorgeous city views. The deep soaking tub was the best part after a long day out. The hotel is situated on the east side of the city, conveniently located just 1.5 miles from Pioneer Courthouse Square and 3 miles from the peaceful Japanese Garden.
For snacks and coffee, I loved the cute little artisan bakery downstairs. There was also an upscale wine bar, a handy convenience shop, and a modern fitness center to keep my routine going. My favorite dining spot was the trendy rooftop restaurant, which gave fine city views with a menu full of creative cocktails and smooth craft beer.
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My personal highlights…
• Enjoying vegan eclairs and warm chai lattes from the cute onsite bakery, Citizen Baker
• On healthier days, sipping a chilled raspberry kombucha with a rooftop view
The Nines Hotel
The Nines Hotel is an upscale design haven in the heart of downtown Portland. It blends art deco elegance with a vast collection of contemporary art. The hotel paid tribute to its original purpose—the building was built in 1909 as the Meier & Frank flagship department store and headquarters.
The lobby featured artistic contributions from a local art college, and the amenities were both stylish and unique. I visited the library-themed cocktail bar, stretched out in the stylish fitness center, and loved the trendy rooftop restaurant, where they served bold Asian fusion dishes with panoramic city views. For casual nights, there was a relaxed casual restaurant offering classic American cuisine.
My room was modern and cozy — equipped with a sleek flat-screen TV, complimentary Wi-Fi, and my favorite: complimentary evening cocktails. The hotel is in the center of everything, conveniently located next to the 6th Ave MAX light rail station and just a ten-minute walk to the Art Museum.
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My highlights…
• Dining at the rooftop Asian restaurant, The Departure Lounge
• Savoring sweet potato miso ramen with hot mulled sake
• Gazing out at Mount Hood as the city lights came on
