Small and compact and not too far from the beautiful Oregon coast, Portland showcases everything great about the hipster scene. Brimming with style, character, a sense of hope, and community, I found myself surrounded by cool little cafes, cheap chic vintage shops, and good-natured, eco-conscious hipsters with hearts. After some exploring, I discovered that Portland’s charmingly unique hotels also reflect the city’s progressive and creative outlook. Here are my favorite hotels in Portland, Oregon, that are cool, quirky, and unusual to help you plan a fun and exciting city break (in no particular order).
McMenamins Kennedy School – A wonderful offbeat hotel set in a restored 1915 elementary school
Built in 1915, this Art Nouveux-era elementary school is literally in a class of its own. With half of its 57 individually designed boutique rooms retaining their original classroom character and the other half literary-themed, the famous and highly rated McMenamins Kennedy School exudes an unusual vintage cool. Luckily, craft beer and freshly roasted coffee take the place of school dinners at this hotel.
Guests can enjoy house ale at the Concordia Brewery (formerly the Girls’ Room), listen to great live music on the premises, and eat delicious, sustainably sourced dishes at the Courtyard Restaurant. After a day exploring all of Portland’s sights, you can relax by the outdoor pool or combine local pub food with movie magic on the auditorium screen. A truly unique and fun Portland hotel experience.
Caravan, The Tiny House Hotel – this unique and singular hotel is one of the best places to stay in Portland
The ‘tiny house hotel is located in Portland’s trendy Alberta arts district. It features six casitas on wheels, ranging from 120 to 170 square feet. Each casita is uniquely designed and fronts an intimate fire pit, perfect for meeting neighbors and relaxing after a long day of exploring.
The style of this unique Portland hotel is eccentric and offbeat, but that’s part of its charm. Of course, there are many beautiful and romantic hotels in Portland. Still, Caravan’s bohemian vibe ensures a cozy and highly enjoyable stay, while the immediate neighborhood boasts interesting restaurants, gastro pubs, bars, and quirky shopping areas.
Jupiter Hotel: A hip, retro-chic Portland boutique hotel converted into a mid-century biker’s lodge
‘For modern travelers, cultural creatives, and anyone who lives outside the box,’ the highly rated Hotel JupiterThe Hotel Jupiter, located in the trendy Burnside area of Portland (a 5-minute drive from downtown), maybe the ideal place for you. If you want to party all night, you can stay on the bar side of the hotel, right next to the Doug Fir Lounge and Restaurant; this award-winning little venue offers excellent food, beer, and live music so you can dance until the wee hours of the night or dawn. But, for a quieter stay, choose a room on the cool side. All rooms feature stylish decor inspired by the 1950s American dream, free Wi-Fi, flat-screen TVs, and everything you need for a comfortable – and fashionable – stay in Portland.
In addition to a cool 24-hour art gallery and a contemporary courtyard with a trendy fire pit, the hotel is dedicated to supporting local artists and small businesses. They host an “artist’s welcome” event on the first Friday of every month, where you can mingle with local artisans and explore multi-sensory art forms with like-minded people. A mid-range Portland hotel ideal for the urban street traveler, it’s a contemporary culture at its finest!
Ace Hotel: A unique and modern hotel in the city’s center, located in a historic building
A little chic and funky, this refreshing Portland hotel is an affordable option without compromising style and comfort. Located in a historic building in downtown Portland (the vibrant heart of the city), the highly rated The Ace Hotel is close to all the sights and with plenty of public transportation links. The spacious rooms are lovingly decorated by local artists and come with free Wi-Fi, minibars, and flat-screen TVs, and homemade, locally sourced food and drink are available in the Clyde Common Restaurant and Bar.
If you feel like exploring the city on two wheels, there are bikes you can borrow or rent a handmade bike created for the hotel by artist Jordon Hufnagel. In addition, there are plenty of welcoming common spaces – including a café and several restaurants – where you can kick back with your fellow travelers, put on a vinyl record, or take advantage of the gorgeous vintage photo booth to capture some vacation memories. Gorgeous!
McMenamins Crystal – a famous historical and themed hotel that is also home to an equally renowned ballroom
Experience downtown Portland at its Rock ‘n’ Roll best at this quirky Portland hotel inspired by The Crystal Ballroom’s long musical history. Housed in a building built in 1911, the décor in each of the 51 rooms at the much-loved and esteemed McMenamins Crystal Hotel is influenced by one of the Ballroom’s most notable acts – from Blondie to The Flaming Lips, local artists and fans. They have gone to great lengths to capture the atmosphere generated by these music icons. You can even be a part of history with the Crystal Ballroom right across the street!
The wonderfully eclectic rooms are also fabulous. With a music theme throughout the hotel, the brightly colored rooms are named after a well-known musician and feature fantastic city views and private bathrooms. Other exciting features are that pets and children under six years old can stay for free, an indoor pool, and a wonderful art gallery, of course with a musical theme. Like all McMenamin hotels, this one is located in a historic building, has its venue, and serves food and beers made with only the best Northwest ingredients. Music lovers, of course, will love this Portland hotel, which even offers limited room and concert packages that are well worth it.
Sentinel Hotel – a creative and refined hotel housed in an elegant historic building
Housed in a historic 1909 terracotta building in the heart of downtown Portland (located directly across a streetcar stop), the exceptionally rated 4-star luxury Hotel Sentinel is a place where creative thinkers, artists, and entrepreneurs can Lay your head down and feel inspired. The fabulous interior is a fusion of old luxury and contemporary ideas with black and white prints of inspiring people and carefully selected 20th-century local art. I stayed on the top floor, with beautiful city views, and had access to the charming “Room at The End Of The Hall,” a relaxing lounge that deliberately inspires creativity. Then, I headed to the state-of-the-art 24-hour fitness center when I wanted to move up a gear.
The food at the hotel’s two luxury restaurants was delicious, and I admired the eco-friendly attitude of this trendy Portland hotel – it even has its beehives on the roof to supply the hotel with local honey! Stylish, pet-friendly rooms offer Wi-Fi and flat-screen TVs; if you opt for a flat-screen, you’ll also find cozy fireplaces. It is a truly innovative mix of luxury and free thinking and a great place to stay when visiting this glittering and quirky city.
Moxy Portland Downtown: A hip, upbeat, offbeat hotel with a youthful, fun vibe
The popular hotel brand now has a fun version of Portland marked with a huge neon sign in Moxy’s signature hot pink color and its usual floor-to-ceiling glass windows. However, inside the Moxy Portland Downtown, the decor is just as fun and flashy, with unique, colorful, and ultra-modern décor that locals and out-of-towners alike seem to love.
The atmosphere is youthful and fun, and its Midtown West End location puts you right next to some of Portland’s best restaurants and shops. Modern rooms feature flat-screen TVs, Wi-Fi, and modern design, and some offer bunk beds. Other services include a trendy pleasant bar and a fitness center.
The Hoxton: A trendy Portland boutique hotel perfect for millennials and Gen Z
The Hoxton is located in the heart of Portland’s historic Chinatown, offering easy access to all city areas by train, taxi, and other public transportation. This boutique hotel is brand new but provides a dichotomy: a mix of modernism with nods to Portland’s storied past.
Tasteful furnishings and retro decorations give the hotel’s interior an attractive color scheme. Large windows let in plenty of natural light. The rooftop restaurant and basement bar serve a wide selection of cocktails, beers, and snacks. It is a comfortable and fresh hotel perfect for travelers.
Duniway Hotel – Portland’s New Hip Contemporary Lifestyle Hotel
Billed as Portland’s newest lifestyle hotel, the exceptionally rated 4-star Hotel Duniway has quickly become one of the most popular places to stay in Portland. Located on a tree-lined street in the heart of downtown Portland, within walking distance of shops, bars, and restaurants, this hotel is a stylish and modern Portland base with high standards.
Sleek, polished rooms have modern decor and plenty of amenities, and the upgraded rooms and suites are especially spectacular. Other hotel highlights include a trendy bar-restaurant run by celebrity chef Chris Cosentino, an indoor pool, a modern gym, and a lush, furnished terrace that regularly hosts live music and yoga classes. The best of Portland.
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