Small and compact and not too far from the beautiful Oregon coastline, the unique Pacific Northwest Port city of Portland showcases everything good about the hipster scene, including its plentiful supply of characterful places to stay. From quirky boutiques to modern, here are my favorites…
1. McMenamins Kennedy School
Located in the Northeast of the city home to an arts and culture scene, and craft breweries. I was a huge fan of this boutique with bold and eclectic decor, a historic building, and eco-positive policies.
My room had vintage-style furniture, parquet floors, a private bathroom, free WiFi, air-con, and complimentary toiletries. I spent the day in the outdoor soaking pool and then dining on pub fare while movies played on the auditorium cinema screen!
It also included a gift shop, surrounding gardens, an onsite restaurant, and four themed bars. I sipped on a house craft brew in the onsite Concordia Brewery (formally the little girl’s room!), listened to live Indie music in the on-site venue, and had a dinner made from locally sourced ingredients in the Courtyard Restaurant.
- To book, check prices or availability for McMenamins Kennedy School
2. Jupiter Hotel
This spot is located Burnside Street, known for its concentration of vintage stores, bars, and nightlife, it’s a major thoroughfare in the city and only a 5-minute drive from Downtown.
I partied in the retro-themed bar next to the hotel’s Doug Fir Lounge and Restaurant, which showcased a rock band in the basement.
It also served up handcrafted cocktails, craft beer, and American eats with vegan and gluten-free options. Back at the hotel, my pet-friendly guest room featured retro-styled décor, free WiFi, a flat-screen TV, and air-con.
As well as a 24-hour art gallery and a contemporary courtyard patio with a trendy fire pit, I love the hotel is dedicated to supporting local artists and small businesses, and on the first Friday of every month, it hosts a ‘reception for the artist,’ an event where you can mix with local artisans and explore multi-sensory art forms with like-minded people.
- To book, check prices or availability for Hotel Jupiter
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3. Ace Hotel
The Ace is a mid-range accommodation option that doubles as a locally famous hangout. It’s located in a historic building in The West End neighborhood which is known for its nightlife, lively bars, restaurants, and independent boutiques.
The overall look is creative, with dark wood and colorful retro-styled furniture. There’s a communal vibe about the place and I easily got casually chatting with quite a few guests.
My guest room, decorated by local artists, had dark wooden floors, the odd exposed brick wall, and plenty of quirky features, like the vinyl record player. Some rooms have shared bathrooms, but all come 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 offers varied innovative menu choices.
Other features include the bespoke handmade motorcycle created for the hotel by artist Jordon Hufnagel, the on-site cafe, and multiple restaurants, where you can chill out with fellow travelers, play a vinyl record or two, or mess around in the vintage photo booth.
- To book, check prices or availability for The Ace Hotel
4. McMenamins Crystal
This hotel is located in a historic building built in 1911 in the buzzy West End part of Downtown. Here, you’ll be surrounded by busy bars, restaurants, cafes, and independent shops. Nearby spots include the famous Powell’s Books, the Pearl District, and Jimmy Mak’s Jazz Club.
I found the vibe relaxed but with eclectic music-themed decor featuring unique artwork, and bright colors. Each of the 51 rooms is influenced by one of the standout shows at the Crystal Ballroom across the road – from Blondie to The Flaming Lips.
I stayed in a themed room with vintage furniture, city views, a private bathroom, free WiFi, plush bathrobes, and organic toiletries.
Other features include an on-site live music venue and weekend comedy shows, a lively bar, two on-site restaurants serving Northwest cuisine and craft brews, an indoor soaking/swimming pool, and an art gallery—music-themed, of course. Oh, and pets and children under six can stay for free!
- To book, check prices or availability for McMenamins Crystal Hotel
5. Sentinel Hotel
This is where the hotel owners say “creative thinkers, artists, and entrepreneurs can lay their heads and be inspired”! It’s housed in a historic terracotta building dating from 1909 in central downtown near a streetcar stop, Powell’s Bookstore, and the Portland Art Museum.
During my stay, I found decor a mix of old-time luxury and contemporary elements with black and white prints of intellects, worn leather sofas, 20th-century local art, and many books!
I stayed in a boutique-style, pet-friendly guest room with free Wi-Fi, a minibar, air-con, a flat-screen TV, luxury linens, and a pillow and iPod menu. The Well & Fit kit kept me busy with a yoga mat, fitness equipment, and a tablet pre-loaded with fitness videos.
Other features included the upscale restaurants on site, a bar with creative cocktails, the eco-friendly ethos, and the beehives on the roof, which supply the hotel with local honey.
The breakfast featured a wide range of organic options, including the house-made honey, which I highly recommend trying!
- To book, check prices or availability for Sentinel Hotel
6. Moxy Downtown
It is located in a central downtown area near the International Rose Test Garden, the trendy Pearl District, and Powell’s Bookstore.
Inside, the modern decor is eye-catching, with pink neon lights, colourful design details, and floor-to-ceiling glass front windows.
I stayed in a guest room that featured a contemporary design, wooden floors, a cable flat-screen TV, air-con, free Wi-Fi, and city views.
Other amenities included a bar serving hand-crafted cocktails, an onsite restaurant with varied breakfast menus and dinners, and a fitness center.
- To book, check prices or availability for Moxy Downtown
7. Hotel Vintage
The 4-star hotel is located in downtown Southwest, near Providence Park and the Pearl District. It is an 11-minute walk from the Portland Art Museum. The hotel is also at the center of a lot of entertainment action.
The overall design is a boutique-style, and the walls are art-adorned. There’s a floating staircase, art sculptures, a graffitied lobby, and chandeliers shaped like bunches of grapes! I stayed in a loft-style guest room with a flat-screen cable TV, a minifridge, plush bathrobes, city views, and yoga mats!
The Pazzo restaurant offers a buffet breakfast, local wines, and Italian cuisine. The Bacchus Bar, located on-site, serves craft beers and wines, as well as old-school arcade games and a pool.
In addition to welcoming pets and offering a modern 24-hour fitness center, the hotel focuses on gastronomy and offers urban tasting sessions in its lounge room bar.
- To book, check prices or availability for Hotel Vintage
8. Duniway Hotel
Billed as the city’s newest lifestyle hotel, it’s located in the Central Business District- within walking distance of independent shops, bars, and restaurants. The Portland Art Museum, the Arlene Schnitzer Concert Hall, and MAX Light Rail are nearby.
The overall design is stylish and trendy with high standards. It featured contemporary furniture, exotic rugs, green plants, and art prints.
I stayed in a spacious guest room with modern decor, free WiFi, high-thread-count linens, a visual doorbell, city views, and an espresso machine.
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 hosts live music and yoga classes.
- To book, check prices or availability for Duniway Hotel
9. Jupiter Next
This is the new sister hotel of the Jupiter Hotel, but it’s an officially higher-graded hotel. It is located on Eastside Burnside Street and is known for its independent boutiques and live music venues. Near Voodoo Donuts and Revolution Hall.
Designed by trendy Works Progress Architecture, the hotel offers views of the city and the West Hills. The design is contemporary, 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, glass bathrooms, a signature knit throw from Seek & Swoon, a voice-activated in-room concierge, high-speed Wi-Fi, and a large flat-screen TV.
The hotel also had space to work, relax, and socialize. The tropical-themed onsite restaurant and bar served American cuisine, breakfast, and cocktails and even turned into a disco in the evenings. There was also an open-air lounge on the fifth floor with city views.
- To book, check prices or availability for Jupiter Next
10. Hoxton Hotel
This boutique hotel is in the city’s historic Chinatown, which has many restaurants, shops, and a MAX Light Rail station. The famous White Stag sign and Tom McCall Waterfront Park are also nearby.
Housed in a restored 1906 building, it has modernist furniture, quirky ornaments, a pastel color scheme, and large windows that let in lots of natural light.
Guest rooms range 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.
Other amenities include a rooftop restaurant that combines American food with views across the city, a coffee shop that offers pastries and coffee, and a speakeasy-style basement bar.
I suggest trying their eatery, which serves up creative cocktails inspired by the local area, craft beers, and snacks.
- To book, check prices or availability for The Hoxton Hotel
11. Hotel Zags
This 4-star hotel is 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.
Other nearby attractions include the city’s Farmer’s Market, South Waterfront Park, and the Hawthorne Asylum Food Cart Pod.
It’s a design boutique inspired by the city’s unique spirit. I loved that it offers retro-modern furniture, contemporary art, and lots of wood and greenery.
My guest room featured a flat-screen cable TV, air conditioning, free Wi-Fi, an iPod dock, and a marble bathroom. All guests receive complimentary passes to a nearby 24-hour fitness center.
Other amenities include the interior courtyard with fire pits, the city’s first-ever living wall, a 24-hour store, buffet breakfast, and an onsite restaurant, Nel Centro, which offers a fine dining experience engineered by the regarded local chef and restaurateur David Machado.
- To book, check prices or availability for Hotel Zags
12. The Heathman
Housed in a downtown historic building from 1927, The Heathman offers a premium boutique lodging experience perfect for couples (it’s a hotel made world-famous by the Fifty Shades of Grey novels!).
Recognized for its distinction and quality, this 4-star property is conveniently close to various cultural attractions, including galleries, parks, and museums. It is a short walk from the Pioneer Square South MAX Station.
This hotel combines traditional charm with contemporary amenities. My room was well-appointed, featuring a flat-screen TV, a French press coffee maker, and complimentary Wi-Fi. The suites include additional comforts such as 4-poster beds, whirlpool tubs, and separate living areas.
The hotel’s facilities include a state-of-the-art fitness center and the Tea Court Lounge, known for its high-quality culinary offerings. I loved the cultural events, such as live Jazz music sessions twice a week and wine tastings during weekday evenings.
- To book, check prices or availability for The Heathman Hotel
13. Hotel Deluxe
The Hotel Deluxe is a 4-star property featuring an Art-Deco design that pays tribute to the cinematic arts. The hotel is decorated with a notable collection of photographs from classic films dating from the 1930s to the 1960s, with different floors dedicated to iconic directors and actors.
In my opinion, it offers a unique experience with its pop-up cinema, where I enjoyed classic films along with a selection of craft beers and cocktails.
The hotel is 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 would highly recommend trying their Afternoon Tea in the grand lobby and enjoying a drink in the lounge, reminiscent of a 1950s cocktail bar!
- To book, check prices or availability for Hotel Deluxe
14. Hotel Eastlund
The Eastlund Hotel is a boutique hotel with a distinctive 1960s-inspired design, situated on the east side of the city, conveniently located 1.5 miles from Pioneer Courthouse Square and 3 miles from the Japanese Garden.
The hotel’s design features a blend of geometrical elements and a palette that nods to 1960s aesthetics, giving it a sophisticated atmosphere.
My room included complimentary Wi-Fi, a flat-screen TV, and panoramic city views. Select rooms also include additional space and soaking tubs for added comfort.
The hotel’s amenities include a convenience shop, a fitness center, and a rooftop restaurant with expansive views of the cityscape and a menu emphasizing local beer selections.
Make sure you try the artisan bakery and a wine bar on-site! The hotel is a convenient base for guests to discover the city’s diverse attractions and unique offerings.
- To book, check prices or availability for the Eastlund Hotel
15. The Nines Hotel
The Hotel Nines, a 4-star establishment, stands out for its distinctive design that pays tribute to the building’s original purpose as the Meier & Frank flagship department store and headquarters in 1909.
I loved how it features artistic contributions from the local art college and a variety of amenities including a library-themed cocktail bar, a contemporary fitness center, a rooftop restaurant offering Asian fusion dishes with panoramic city views, and an additional restaurant that specializes in American cuisine.
My room was equipped with a flat-screen TV and complimentary Wi-Fi, with select rooms offering the added perk of complimentary evening cocktails.
Located in the center of downtown, this hotel is conveniently located 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
