Top 20 Cool and Unusual Hotels in Portland 2023

Small and compact, and not too far from the beautiful Oregon coastline, Portland showcases everything which is good about the hipster scene.

Bursting with cool style and character and a sense of hope and community you’ll be surrounded by cool little cafes, chic and cheap vintage shops, and good-natured, eco-minded hipsters with a heart.

Its charmingly unique places to stay also reflect the city’s progressive and creative outlook on life. Here is a collection of my favorite cool, quirky and unusual hotels in Portland, Oregon to help you plan a fun and interesting city break (in no particular order, they’re all awesome)…

1. McMenamins Kennedy School – a wonderful offbeat hotel set in a restored 1915 elementary school

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!

• Address: 5736 NE 33rd Ave, Portland, OR 97211
• To book, check prices or availability for McMenamins Kennedy School

2. Jupiter Hotel – a hip retro-chic Portland boutique hotel converted from a midcentury motor lodge

‘For modern travelers, cultural creatives and anyone who lives outside the box’ the highly-rated Hotel Jupiter Portland, located in the hip and happening Burnside area of Portland (a 5-minute drive from Downtown), maybe 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.

A perfect hip mid-range Portland hotel for the streetwise urban traveler, this is contemporary culture at its best!

• 800 E Burnside St, Portland, OR 97214
• To book, check prices or availability for Hotel Jupiter Portland

3. Ace Hotel – a unique and trendy downtown hotel set in a historic landmark property

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 Portland 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 cozy communal spaces – including a funky onsite cafe and multiple cool restaurants – where you can chill out with fellow travelers, play a vinyl record or two or take advantage of the gorgeous vintage photo booth to capture some old-style holiday memories! Wonderful!

• Address: 1022 SW Harvey Milk St, Portland, OR 97205
• To book, check prices or availability for The Ace Hotel Portland

4. McMenamins Crystal – a famously cool and themed historic downtown hotel which is also home to an equally famous ballroom

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 colored 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!

• Address: 303 SW 12th Ave, Portland, OR 97205
• To book, check prices or availability for McMenamins Crystal Hotel

5. Sentinel Hotel Portland – a creative and refined downtown hotel housed in an elegant historic building

The luxurious 4-star exceptionally rated Sentinel Hotel Portland is housed in a historic terracotta building dating from 1909 in the heart of downtown Portland (set directly at a streetcar stop) and is a place where creative thinkers, artists, and entrepreneurs can lay their heads 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.

The food in the hotel’s two upscale restaurants was delicious and you’ll admire 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 suite and you’ll find cozy 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. 

• Address: 614 SW 11th Ave, Portland, OR 97205
• To book, check prices or availability for Sentinel Hotel Portland

6. Moxy Portland Downtown – a funky, upbeat and unconventional hotel with a youthful fun vibe in a great downtown location

The hugely popular hotel brand now has a funky Portland version marked out with a huge neon sign in Moxy’s signature hot pink and its usual floor-to-ceiling glass front windows.

Inside the Moxy Portland Downtown the decor is equally as fun and striking with unique, colorful, and ultra-modern decor with both locals and visiting out-of-towners seem to love.

The vibe is youthful and fun and the cool location in Downtown’s West End will put you side-by-side with some of the best eating and shopping in Portland.

The trendy guest rooms feature flat-screen TVs, Wi-Fi, a modern design and some offer bunk beds. Other amenities include a hip sociable bar and a fitness center.

• Address: 585 SW 10th Ave, Portland, OR 97205
• To book, check prices or availability for Moxy Portland Downtown

7. Hotel Vintage – creative-themed upscale accommodation which is often said to be one of the best hotels in Portland

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 Portland is a pioneering upscale hip boutique hotel that 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 center, 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!

• Address: 422 SW Broadway, Portland, OR 97205
• To book, check prices or availability for Hotel Vintage Portland

8. Duniway Hotel – Portland’s trendy new contemporary lifestyle hotel

Billed as Portland’s newest lifestyle hotel the 4-star exceptionally rated Duniway Hotel Portland 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 easy walking distance of cool shops, bars, and restaurants galore – this is a 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 a super-lush furnished terrace that regularly hosts live music and yoga classes. Upscale Portland at its best!

• Address: 545 SW Taylor St, Portland, OR 97204
• To book, check prices or availability for Duniway Hotel Portland

9. Jupiter Next – a hipster-friendly retro-chic boutique hotel located in the trendy Central Eastside district

This new urban chic hotel in Portland’s Eastside can be seen as an embodiment of the city’s hipster culture.

Designed by Works Progress Architecture, Jupiter Next Portland combines edgy with luxury and really, really stunning views of the city and the West Hills.

The vibrant arts, culture and tech scene of the Eastside is just outside the door, and you can get the bus or streetcar to downtown.

The modern vibe is everywhere, from the landmark metal staircase in the lobby, designed by Laura Sol, to the seating in the Secret Garden terrace.

The cozy bedrooms have city-inspired headboards and signature knit throws from Seek & Swoon on the beds.

There’s space to work, relax and socialize in the hotel, and the tropical-themed bar Hey Love turns into a disco in the evenings.

• Address: 900 E Burnside St, Portland, OR 97214
• To book, check prices or availability for Jupiter Next Portland

10. Hoxton Hotel Portland – a hip and trendy boutique hotel with a popular rooftop restaurant perfect for Millennials and Gen Zs

The Hoxton Hotel Portland is set in the heart of Portland’s historic Chinatown and provides easy access to all areas of the city by rail, taxi, and other public transport. This boutique hotel is a fresh new build yet provides a dichotomy: a mixture of modernism with nods to Portland’s historic past.

Tasteful and plush furnishings blend well with retro ornaments to give the hotel’s interior an appealing color scheme. Large windows let in tons of natural light.

A rooftop restaurant provides exhilarating views across the city, while the basement bar serves up a wide selection of cocktails, beers, and snacks. It’s a comfortable, cool hotel perfect for all types of travelers.

• Address: 15 NW 4th Ave, Portland, OR 97209
• To book, check prices or availability for The Hoxton Hotel Portland

11. Hotel Zags – a stylish retro-chic Portland boutique hotel perfect for Instagrammers

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 Zags Portland 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 center.

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!

• Address: 515 SW Clay St, Portland, OR 97201
• To book, check prices or availability for Hotel Zags Portland

12. Hotel Vance – a funky new downtown Portland hotel which features colorful murals and industrial accents

Hotel Vance Portland is dedicated to the innovation and creativity that have made Portland what it is, and the name itself is short for “Advance”. It’s also one of the most convenient places to stay in Portland, located downtown near the Pearl District and well connected to other parts of the city.

The sleek, futuristic shape of the building is echoed in the decor. Rooms have free WiFi, city views, and artwork that evokes Portland’s appellation as the City of Roses.

There’s a Starbucks in the hotel and also the Beastro by Marshawn Lynch, which serves Hawaiian food during the day and Korean in the evenings.

• Address: 1455 SW Broadway, Portland, OR 97201
• To book, check prices or availability for Hotel Vance Portland

13. Hotel Grand Stark – one of the coolest boutique hotels in Portland located within Portland’s vibrant Central Eastside

In keeping with the Palisociety tradition of fitting each hotel to its locale and history, the Hotel Grand Stark embodies the Pacific Northwest spirit of quirky, independent do-it-yourself.

Located in the Central Eastside, it is close to the area’s best cafes, bars and restaurants, as well as the artists and craftsmen who give the neighborhood its character.

The distressed-chic lobby wall, lovingly-displayed artwork, and bespoke emerald green accents make this a truly Instagrammable hotel.

The understated luxury of the rooms is enhanced with Nespresso coffee machines, SMEG refrigerators, plush robes and  Diptyque bath products.

The Bar Chamberlain is a classic hotel bar, but with a millennial twist, serving Avocado Toast for breakfast as well as classic cocktails Steak Au Poivre in the evenings.

• Address: 509 SE Grand Ave, Portland, OR 97214
• To book, check prices or availability for Hotel Grand Stark

14. The Heathman Hotel – a fabulous upscale design hotel made world-famous by the Fifty Shades novel

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 The 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 center, an intimate Tea Court Lounge offering delicious fine dining, live Jazz twice a week, and complimentary wine tastings offered on weeknights. 

Address: 1001 SW Broadway, Portland, OR 97205

• To book, check prices or availability for The Heathman Hotel 

15. Hotel Deluxe – old-school Hollywood glamour with an art-deco theme

Film buffs will love this place. The 4-star exceptionally rated Art-Deco Hotel Deluxe Portland is a dream exuding the glamour of Hollywood’s 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 1930s through to the 1960s 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 colors, polished wood and a timeless elegance.

Make sure you go for Afternoon Tea in the opulent lobby and a creative cocktail in the 1950s-style cocktail lounge! 

• Address: 729 SW 15th Ave, Portland, OR 97205
• To book, check prices or availability for Hotel Deluxe Portland

16. Hotel Eastlund – a vibrant and trendy upscale boutique hotel in Portland

Situated in the heart of the bustling east side 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 Eastlund Hotel Portland sports a gorgeous and sophisticated 1960’s esque design full of geometrical shapes and 1960’s chic shades.

The chic and colorful 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 center, 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!

An awesome place from which to explore everything cool and unusual that Portland has to offer!

• Address: 1021 NE Grand Ave, Portland, OR 97232
• To book, check prices or availability for the Eastlund Hotel Portland

17. Staypineapple at Hotel Rose – a hip, modern Portland hotel with colorful kitsch-style decor

Staying at a Staypineapple Hotel is always a thoroughly decent experience and the highly-rated Staypineapple at Hotel Roseis 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 the city, waterfront, and park.

You’ll have access to the gym, freebie coffee and cookies in the afternoon, and superb in-room amenities such as an iPhone dock/ Bluetooth speaker, big TV, and super comfy bedding.

Other hotel highlights include the hotel’s vintage yellow cruiser loaner bikes and the fact that pets can stay too (for a reduced fee if you book the pineapple pup package) – great work Staypineapple!

• Address: 50 SW Morrison St, Portland, OR 97204
• To book, check prices or availability for Staypineapple at Hotel Rose

18. Hotel Monaco – a chic, trendy and very Instagrammable downtown Portland hotel

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 at Hotel Monaco Portland 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 whiskey 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!

• Address: 506 SW Washington St, Portland, OR 97204
• To book, check prices or availability for Hotel Monaco Portland

19. The Nines Hotel – a 5-star hotel luxury hotel with a chic and opulent design

The exceptionally rated 4-star Hotel Nines Portland is seriously a masterpiece in design where luxury and elegance triumph throughout in a perfect homage to Meier & Frank who brought the building to life in 1909 as their flagship department store and headquarters.

Also expect artwork supplied by the local art college, a library-themed cocktail bar, a modern fitness center, a rooftop restaurant serving Asian fusion cuisine combined with sublime city views, and an onsite restaurant which served up hearty American cuisines and ultra-chic rooms with flat-screen TVs and Wi-Fi. Upgraded rooms with complimentary evening cocktails!

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.

• Address: 525 SW Morrison St, Portland, OR 97204
• To book, check prices or availability for Hotel Nines Portland

20. The Lion and The Rose – a characterful guesthouse with quirky-chic vintage-inspired decor

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.

Expect quirky decor such as antique paintings, woven rugs, a porcelain bathtub standing on golden lion’s feet upon a polished marble floor, a wraparound porch, blends of tea on offer and plenty of nostalgia – a unique Portland gem! 

• Address: 1810 NE 15th Ave, Portland, OR 97212
• To book, check prices or availability for The Lion and the Rose Guest House

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