A unique hotel in Portland Oregon

Top 20 Cool And Unusual Hotels In Portland 2023

42 mins read

Small and compact, and not too far from the beautiful Oregon coastline, the unique Pacific Northwest Port city showcases everything which is good about the hipster scene.

When I visited it was honestly one of my favorite cities I’d traveled to. It was bursting with cool style and character and a sense of hope and community. I found myself surrounded by cute little cafes, chic and cheap vintage shops, and good-natured, eco-minded hipsters with a heart. 

Its charming and interesting collection of places to stay also reflect the city’s progressive and creative outlook on life. Here are 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 equally awesome)

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

A fun hotel to stay in Portland

A very cool hotel to stay in Portland

Built in 1915, this repurposed Art Nouveux-era elementary school is a class of its own, literally!

McMenamins Kennedy School is located in the Northeast of the city which has more of a local neighborhood feel. Some highlights of this area include a vibrant arts and culture scene, plenty of craft breweries, bike lanes, green spaces, quirky cafes, and interesting independent boutiques.

It’s also near the Moda Center and the Veterans Memorial Coliseum. Alternatively, it’s easy to get downtown via the popular MAX light rail system or bus.

The decor, building, and concept are just so unique and I loved my stay here. Half of the 57 individually designed boutique rooms maintain their original classroom character and the other half sporting literary themes. The vibe is relaxed and friendly but it radiates an unusual vintage cool too.

Guest rooms are adorned with authentic vintage-chic decor and design features like hardwood or parquet floors as well as private bathrooms, free WiFi, air-con (or heating!), free toiletries, and comfy beds.

More of a retreat than a hotel after a day exploring the city, you can unwind in the outdoor soaking pool or combine homegrown pub fare with movie magic on the auditorium cinema screen! Or just take a wander around the cute gift shop, beautiful green gardens, hip onsite restaurant, and no less than four themed bars! 

Thankfully craft beer and freshly roasted coffee replace school dinners in this hotel! Guests can enjoy the house brew in the hotel’s very own 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.

Overall I thought it was a truly unique and fun gem of a place!

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

A retro hotel in Portland

A creative hotel in Portland

Aimed at ‘modern travelers, cultural creatives, and anyone who lives outside the box’ the highly-rated Hotel Jupiter, is a great choice for a hipster-friendly stay.

It’s located in the trendy Burnside Street which is a major thoroughfare in the city and only a 5-minute drive from Downtown. The eclectic area is filled with quirky shops, great nightlife, tasty eateries, cool cafes, and vintage stores. It’s a fun place to base yourself while also being very accessible to major attractions.

If you want to party the night away you can stay on the bar side of the hotel, right next to the hotel’s Doug Fir Lounge and Restaurant which serves up creative cocktails and tasty American eats with vegan and gluten-free options. It’s a very cool spot with a great vibe (I was a big fan!) and this award-winning small venue offers excellent food, beer, and live music so you can rock until the small hours! The live music gigs here are very popular and attract a fun crowd.

For a more peaceful stay choose a room on the chill side. All guest rooms are pet-friendly and feature funky and chic 1950’s American dream-inspired décor, free WiFi, flat-screen TVs, air-con, and everything else you need for a very comfy – and trendy – stay.

As well as a 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 on 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.

Overall I thought this perfect mid-range hotel for the streetwise urban traveler who also likes to party. Although shy and retiring types may want to give this one a miss! 

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

A unique hotel in Portland Oregon

A hipster hotel in Portland USA

This funky spot is an affordable option without compromising on style and comfort and also doubles as a locally famous hangout for the cool kids in the city.

The highly-rated The Ace Hotel is based in a historic building in a trendy part of downtown – The West End neighborhood. This area is known for its great nightlife, buzzing bars and restaurants, and trendy Indie boutiques. Culture vultures will also love art galleries, museums, theaters, and live music venues, and it’s also close to plenty of public transport links as well as the famous Powell’s City of Books and the funky Pearl District.

The overall decor is very hip with dark woods and colorful retro-styled furniture and there’s a sociable, communal vibe about the place – I personally got casually chatting with quite a few guests.

The guest rooms range from small to spacious and are lovingly decorated by local artists. There are dark wooden floors, the odd exposed brick wall, and plenty of creative and quirky features such as vinyl record players. Although the style is rustic-chic and some have shared bathrooms. Although all come with free WiFi, minibars, and flat-screen TVs.

Feeling hungry? Then you can enjoy home-cooked locally sourced food, a tasty continental breakfast fand a huge range of alcoholic drinks in the cozy Clyde Common restaurant and bar overseen by Chef Carlo Lamagna who goes all out with innovative menu choices. 

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 (I loved this!)

I also loved that 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!

Overall I thought it was just so different, creative, and art-filled and for a unique mid-range stay downtown, it’s a great choice. 

4. McMenamins Crystal – a famously cool and themed historic downtown hotel with a famous ballroom

A unique stay in Portland

Unique accommodation in Portland

Enjoy downtown at its Rock ‘n’ roll finest at this quirky hotel inspired by The Crystal Ballroom’s extensive musical history. 

The much loved and highly rated McMenamins Crystal Hotel is set in a historic building built in 1911 in the fashionable and buzzy West End part of Downtown. You’ll find yourself surrounded by busy bars, restaurants, cafes, and interesting shops too. Stand-out nearby spots include the famous Powell’s Books, the funky Pearl District, the Artists Repertory Theater, Voodoo Doughnuts, and Jimmy Mak’s Jazz Club.

The décor is fun, whimsical, and most definitely music-themed. I loved that the vibe is cool but relaxed with a shabby-chic kind of feel, with plenty of interesting quirky features, unique artwork, and bright colors thrown in. 

Each of the 51 rooms is influenced by one of the standout shows 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 guest 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 great city views and private bathrooms. Mod cons include free WiFi, comfy bathrobes, and organic toiletries.

Other stand-out features include their very own live music venue and weekend comedy shows, two onsite restaurants and a bar that serves up food made from only the finest Northwest ingredients and popular craft brews, a funky indoor soaking/swimming pool, and a wonderful art gallery – music-themed of course. Oh and pets and children under 6 are able to stay for free.

Overall I was a big fan and music lovers, in particular, will especially adore this place! 

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

An elegant boutique hotel in Portland

A cool boutique hotel in Portland

The luxurious 4-star exceptionally rated Sentinel Hotel is a place where creative thinkers, artists, and entrepreneurs can lay their heads and be inspired! 

It’s housed in a historic terracotta building dating from 1909 in the heart of downtown so the center of all the action. A streetcar stop is directly outside so you’ll be able to explore the city easily including the Pearl District and the South Waterfront. Alternatively, there are lots of interesting places in walking distance including the famous bookstore Powell’s, Portland Art Museum, Oregon History Museum, and shops, restaurants, and cafes galore!

Inside the wonderful interior is a fusion of old-time luxury and contemporary ideas with black and white prints of inspirational people, worn leather sofas, thoughtfully curated 20th-century local art, and plenty of books (my favorite part!)

The elegant pet-friendly guest rooms have a feel of classic upscale elegance and some are very spacious. They all offer free Wi-Fi, minibars, air con, flat-screen TVs, luxury linens, a pillow menu, iPod menu, and opt for a suite and you’ll find cozy fireplaces too. My favorite detail though was the Well & Fit kit which kept me busy with a yoga mat, fitness equipment and a tablet pre-loaded with fitness videos – wow! 

The food in the hotel’s two upscale restaurants was delicious and can be washed down by creative cocktails if you wished. I also admired the eco-minded ethos of this hip hotel – it even has its own beehives on the roof to supply the hotel with local honey! The breakfast was one of the best I’d had in the city – must have been all those organic ingredients! 

Overall I thought this was a gorgeous and innovative combination of luxury and free thinking and a great option when visiting this brilliant and quirky city. 

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

6. Moxy Downtown – funky, upbeat, and unconventional accommodation with a youthful fun vibe

Funky hotel in Portland

Party hotel in Portland

The hugely popular and very Instagrammable hotel brand now has a funky Portland version marked out with a huge neon sign in Moxy’s signature hot pink! 

The Moxy Downtown is located in a great central downtown area within walkable distance of many great attractions including the International Rose Test Garden, the trendy Pearl District, Portland Art Museums, and Powell’s Bookstore. You’ll also be spoilt for choice for nearby independent boutiques, cool cafes, excellent restaurants, Food Carts, and some great craft breweries too. 

Inside the ultra-modern decor is equally as fun and striking with unique, colorful, and funky design details with both locals and visiting out-of-towners seem to love. With a playful, youthful vibe expect neon lights, and floor-to-ceiling glass front windows – as a fan of unique design hotels I loved it!

The trendy guest rooms (there are 197 of them) feature retro-chic wooden floors, flat-screen TVs, cable TVs, air-con, free Wi-Fi, a modern design, city views, and some offer bunk beds. 

Other amenities include a hip sociable bar serving up funky hand-crafted cocktails, an onsite restaurant serving up both tasty breakfasts and dinners, and a trendy-looking fitness center.

Overall if you fancy staying at a funky place with a youthful vibe that will look good on your Instagram, then this is the place for you. Those looking for more tranquil stays should look elsewhere though!

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

7. Hotel Vintage – creative-themed upscale accommodation with a vintage-chic design

A gorgeous boutique hotel in Portland USA

Funky hotel in Portland

Best Luxury hotels in Portland

This is a beautiful, stylish, and striking boutique hotel great for both couples and solo travelers looking for a unique stay.

The 4-star exceptionally rated Hotel Vintage is located in a fabulous downtown SouthWest area location in the center of a lot of entertainment action just half a mile from Governor Tom McCall Waterfront Park on Willamette River, near Pioneer Place Mall (with interesting shops galore), Providence Park, the hipster haven Pearl District and a mere 11-minute walk from the Portland Art Museum. 

The overall feel is chic, creative, and art-adorned. It features delightful design details such as a floating staircase, gorgeous sculptures, a graffitied lobby, and chandeliers shaped like bunches of grapes!

The upscale guest rooms are equally as fabulous with flat-screen cable TVs, minifridges, plush bathrobes, great views, and handy yoga mats! Upgraded rooms come with hot tubs, balconies, or even blissful outdoor hot tubs.

The Pazzo restaurant offers tasty breakfasts, 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 (my favorite bit!)

As well as welcoming pets and offering a modern 24-hour fitness center, the gorgeous abode prides itself on its gastronomy and offers urban tasting sessions in its exquisitely designed lounge room.

Overall I thought this was a great upscale boutique stay, perfect for romance! 

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

8. Duniway Hotel – the city’s new trendy new contemporary lifestyle retreat

One of the best boutique hotels in Portland

An amazing boutique hotel in Portland

Billed as the city’s newest lifestyle hotel the 4-star exceptionally rated Duniway Hotel has quickly become one of the most popular places to stay in the city.

It’s located on a lovely tree-lined street in the hip and happening heart of downtown in the buzzy business district- within easy walking distance of cool shops, bars, and some excellent restaurants. Nearby you’ll find Portland Art Museum, Moda Center, the Arlene Schnitzer Concert Hall, and MAX Light Rail for easy access to the rest of the city.

The overall design is stylish and trendy with high standards. Expect contemporary furniture mixed with exotic rugs, green plants, and trendy prints. I loved the classy but not too over-the-top feel of the place. 

The sleek and polished rooms (all 327 of them) feature trendy decor and lots of mod cons, and the upgraded rooms and suites are particularly spectacular. All have free WiFi, high thread count linens, visual doorbells, great views, and espresso machines. 

Other hotel highlights include a hip onsite restaurant run by celebrity chef Chris Cosentino and an onsite eatery and bar. Collectively they serve up innovative cuisine, creative craft cocktails based on 60 herbaceous spirits, and tasty quick bites.

Add to this an indoor swimming pool, a modern gym, and a super-lush furnished terrace that regularly hosts live music and yoga classes and you have a rather gorgeous upscale boutique stay! 

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

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

Industrial Chic hotel in Portland

Retro cool hotel in Portland

This new urban chic hotel is the sister hotel of the very popular Jupiter Hotel but with slightly more luxurious features. 

The four start exceptionally rated Jupiter Next city’s located Eastside can be seen as an embodiment of the city’s hipster culture. It enjoys a cool and fashionable location on Burnside Street one of the trendiest spots in town with an eclectic mix of independent boutiques, cafes, bars, restaurants, and live music venues. You can easily walk to the famous Voodoo Donuts, Revolution Hall, and Powell’s Bookstore. Alternatively, you can hop on a bus or a streetcar and start to explore.

Designed by trendy Works Progress Architecture, the hotel combines edgy with luxury and really, really stunning views of the city and the West Hills. There’s more than a hint of industrial chic with unique features such as a striking concrete-and-steel staircase (I loved this stunning design piece by Laura Sol), a concrete fire pit, and lashings of black and glass.

The striking and trendy guest bedrooms have city-inspired headboards, large windows, modern art, unique glass bathrooms, signature knit throws from Seek & Swoon, and great mod cons such as a voice-activated in-room concierge, high-speed Wi-Fi, and large flat-screen TVs. It’s a seriously cool place! 

There’s also plenty of space to work, relax and socialize in the hotel, and the tropical-themed and very Instagrammable onsite restaurant and bar serves up creative fine fayre, a tasty breakfast, fun cocktails and even turns into a disco in the evenings so perfect for partygoers. Although if you’re looking just to chill out and gaze at city views then head to the impressive open-air lounge on the fifth floor. 

Overall I thought this is a wonderful trendy urban retreat in a fabulously hip part of town.

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

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

Best hotels in Portland

The Hoxton - best luxury hotel in Portland

Top hotels in Portland

This gorgeous and very hip boutique hotel is a fresh new build yet provides a mixture of modernism with nods to Portland’s historic past.

The 4-star exceptionally rated Hoxton Hotel is set in the heart of the city’s historic and lively Chinatown in downtown of the city and provides easy access to other areas by rail, taxi, and other public transport. You’ll also be surrounded by plenty of great restaurants, unique shops as well as a handy MAX Light Rail station. The famous White Stag sign and Tom McCall Waterfront Park are nearby.

Housed in a restored 1906 building the style is tasteful and plush modernist furniture which blends well with retro-chic design details and quirky ornaments and an easy-on-the-eye color scheme. I especially loved the laid-back vibe and large windows which let in tons of natural light.

Guest rooms come in a range of sizes from ‘snug’ to spacious and all are stylish and trendy with dark woods, funky art, flat-screen TVs, free WiFi, air-con, tall windows offering great city views, and cool black-tiled private bathrooms.

There are great onsite eating options my favorite was the fashionable local hangout and a rooftop restaurant which provides great food accompanied with wonderful views across the city.

Alternatively, there’s a coffee shop that serves up pastries and great coffee, a stylish lounge bar the buzzy speakeasy-style basement bar, and an eatery that serves up a wide selection of cool cocktails inspired by the local area, craft beers, and tasty snacks.

Overall I thought this was a beautiful and trendy boutique perfect for a hip crowd!

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

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

Hotel Modera - a great hotel in Portland

Hotel Modera - one of the best places to stay in Portland

Blending clean sleek lines and welcoming warmth this gorgeous contemporary pet-friendly accommodation promises to offer everything required for a modern and refined boutique stay in the heart of town.

The 4-star highly rated Hotel Zags is situated along Willamette River right in the middle of the funky arts district in downtown just two blocks from a MAX light rail station and a 6-minute walk from 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 styled on the city’s unique brand of style and spirit. Expect retro modern furniture mixed with contemporary art and lashings of wood and greenery. I loved that it was visually stunning and zen-like at the same time! 

The chic and trendy guest rooms come with mod cons such as flat-screen cable TVs, air-con, free Wi-Fi, iPod docks, and plush marble bathrooms. All guests receive free passes to a nearby 24-hour fitness center.

My favorite highlight was the beautiful interior courtyard which comes complete with trendy fire pits and the city’s first-ever (and very green) living wall. There’s also a handy 24-hour store and a tasty breakfast.

It’s also a great place to begin your exploration of the city’s renowned foodie scene as its onsite restaurant Nel Centro offers a fine dining experience engineered by celebrated local chef and restaurateur, David Machado. 

If unique chic and funky elegance is your thing, this may be your perfect boutique stay!

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

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

Instagrammble Hotel in Portland

Hotel Vance Portland

Fun and funky hotel in Portland

The 4-star exceptionally rated Hotel Vance is dedicated to the innovation and creativity that have made this city what it is, and the name itself is short for “Advance”.

It’s also located in one of the most convenient places to stay, located downtown near the Pearl District and well connected to other parts of the city. Portland’s Farmer Market, Powell’s Bookstore, Food Cart Pods, and Providence Park are all nearby.

The sleek, futuristic shape of the building is echoed in the decor. The interior design is both funky and innovative with geometrical shapes everywhere, plenty of steel, bright modern furniture, and unique art.

The pet-friendly guest rooms are equally as creative and eye-catching and come with free WiFi, city views, flat-screen TVs and trendy artwork, private bathrooms, coffee machines, room service and air-con.

Still want more? 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. The breakfasts are very tasty too!

Overall I thought this was a vibrant, creative and unique stay perfect for visiting Millenials and Gen Zs.

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

13. Hotel Grand Stark – one of the coolest boutiques located in the vibrant Central Eastside

Cool Boutique hotel in Portland

Hip hotels in Portland

Trendy Boutique hotel in Portland

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, OR 97214
  • To book, check prices or availability for Hotel Grand Stark

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

Upscale romantic hotel in Portland

Heathman Hotel in Portland

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 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, OR 97205

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

A unique hotel in Oregon

Chic accommodation in Oregon

Film buffs will love this place. The 4-star exceptionally rated Art-Deco Hotel Deluxe 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 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, OR 97205
  • To book, check prices or availability for Hotel Deluxe

16. Hotel Eastlund – a vibrant and trendy upscale boutique with bright and funky decor

A trendy hotel in Portland

A cool and creative 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 Japanese Garden), this boutique design hotel was a real find.

The interior of the 4-star exceptionally rated Eastlund Hotel sports a gorgeous and sophisticated 1960’s esque design full of geometrical shapes and 1960s 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, OR 97232
  • To book, check prices or availability for the Eastlund Hotel

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

Staypineapple at Hotel Rose - one of the best places to stay in Portland

Fun hotel in Portland

Staying at a Staypineapple Hotel is always a thoroughly decent experience and the highly-rated Staypineapple at Hotel Rose 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 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!

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

A chic hotel in Portland

Cool Portland accommodation

Located in downtown (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 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 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, OR 97204
  • To book, check prices or availability for Hotel Monaco

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

A beautiful design hotel in Portland

A cool hotel in Oregon

The exceptionally rated 4-star Hotel Nines 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 that 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 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, OR 97204
  • To book, check prices or availability for Hotel Nines

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

A hip bed and breakfast in Portland

Located a 10-minute walk from an Avenue MAX Station, this is no ordinary 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! 

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