I just love staying in hotels, even in my own home town! I’m sure many of us have become fans of the staycation and if I’m going to be completely honest, I’ve been doing it for many years. It’s the perfect way to pamper yourself and pretend you’re traveling during those times when you can’t, for whatever reason (*cough*pandemic*cough*).
I’ve stayed in every one of these hotels, so this is not simply a regurgitated list of all of the other “best of” lists you will see out there. These are my personal opinions and I will be the first to tell you that each of these properties is superbly and authentically Portland.
The Rose City has more than its share of fun and funky hotels – it’s kind of what we’re known for! Each of these properties have their own unique definition of hospitality, and I will tell you why.
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Canopy by Hilton
I don’t normally subscribe to big chain hotels, just because they are so sterile and have zero character. But Hilton has created their Canopy brand that offers that extra little something in the way of design and amenities that just made me fall in love with the place. They also have a really amazing Hilton Honors Points program that makes it easy to accumulate points, with a welcome amenity at each check in.
The design is cozy chic – think Pottery Barn-style furniture, with Pendleton style accents. The bed and the shower were amazing – both very important to me in every hotel I visit. They have that awesome sliding barn door separating the bedroom from the bathroom/changing area that you see in all of the design catalogs these days. The bed is heaven to sleep on. But the raison d’être is most definitely the Nespresso machine!
The Benson
The crown jewel of hotels in Portland, this is an iconic property listed on the National Register of Historic Places. Many past Presidents have stayed here, and the décor in the lobby is classic wood-paneled elegance at its finest. As you walk in, there is the hotel restaurant and bar to your right, a large and elegantly-furnished sitting area to your left, with hotel check-in directly ahead. This property is also part of the Hilton portfolio.
Once you reach your room, the décor changes abruptly and you are greeted with light muted tones and modern furnishings. An older property, it has clearly received many a facelift, but the bathrooms have been tastefully updated with great showers and luxurious bath amenities. Be sure to walk down the back stairwell – it is almost an museum/art gallery unto itself and offers a pictorial journey down memory lane.
Jupiter NEXT
This is the newest iteration of the Jupiter Hotel directly next door. The NEXT opened their doors back in 2018 and is more modern and fresh-looking than the original Jupiter Motel. Portland’s Doug Fir Lounge is one of the best intimate music venues in town, with a restaurant and bar, and is situated in between the two properties. “The Next” is a more elevated property, and as such, offers great views of Portland’s inner east side and downtown across the river.
With its freshly hip vibe, it screams Portland. My room was very spacious and tastefully decorated, with accent walls and scenes of a vintage Portland. And in classic Portland style, they offer add-on packages such as pet-friendly amenities, and an “explorer kit” for couples!
Inn at Northrup
I love this fun and funky spot in Portland’s trendy Nob Hill neighborhood. Every room is a suite – very spacious, with a mini kitchen, full fridge, and kitchen utensils for cooking meals, which can save you money when you aren’t tempted by the plethora of dining opportunities in the area. The location is one with delicious restaurants everywhere and some of the best shopping in Portland.
This hotel offers a simple, complimentary breakfast, with a Keurig coffee maker in the room. I love this hotel because it has room to spread out; a sitting area with retro furnishing, a desk with an amazing ergonomic chair, and two TV’s (one by the bed and one in the ‘office’ area). In addition, they are almost always offering great deals – it’s a fantastic price for what you get in this section of Portland.
Hotel Zags
Located in the heart of downtown near Portland State University, this is a trendy property where the staff works hard to make your stay the best possible. Upon check in, you will see a sort of a caged in area to your right – that’s where you can check out anything from sports equipment to bikes for use during your stay. They even rent out mini polaroid-style cameras!
Up in the guest room, relax in modern luxury in a room or suite. The city and garden views are awesome, and amenities include a work desk, bath robes, designer linens, mini fridge, coffee maker, and all natural bath products. Just be aware, this is an older property, so the walls are not insulated and you may hear your neighbors!
McMenamins Crystal Hotel
As you may know, I’m ga-ga over the local McMenamins franchise. The Crystal Hotel is another one of their signature funky properties located smack dab in the west end of downtown Portland, just steps from the famous Powell’s book store. I’ve stayed here a couple of times, and the rooms are quintessentially McMenamins, and the Crystal has a music theme, by naming all of their rooms after local musicians.
I highly recommended the Sleater-Kinney corner room, with a great view of downtown Portland. Their soaking pool is one of the best in town, and you can make a night of it by eating at the Zeus Café on property (they have great breakfasts, as well!), then slipping downstairs to have a nightcap at Al’s Den, or head just down the street to one of the city’s best music venues, the McMenamin’s Crystal Ballroom.
Heathman Hotel
The Heathman is also listed on the National Register of Historic Places. I’m going to be completely honest here and say that while I had a pleasant stay, it is probably on the bottom of this Top 10 list. The room was modernly furnished and quiet, but I had trouble with the wifi, and the maid knocked on my door not 10 minutes after I got in the room. She didn’t seem to know that I had just checked in (don’t they keep records of that?) The walls are also thin, so I clearly heard by neighbors (ahem).
Having said that, I had a nice city view on the top floor and the shower was amazing! Nice bath toiletries, French press coffee and tea in the room, and the front desk staff were friendly and quick to respond, complete with a digital concierge. The Heathman is a Portland institution so I will definitely give them another chance in the future.
Tiny Digs Hotel
For true minimalist Portland living, this is a cozy circle of tiny houses gathered around a central fire ring in order to encourage social activity – it’s a great concept! Every tiny house is unique with its own layout, and I was fortunate enough to be able to tour most of them during one of their familiarization tours. I stayed in the Caboose and it was fabulous! It was like staying in a stylish little barn with an alcove bed!
I love tiny houses and have stayed in several over the years. You are supplied with coffee, tea and a few condiments for your meals to cook in the tiny but fully stocked kitchen. It was so rustic and right in the heart of the city – a nice juxtaposition of environments. Occasionally the owners will book live music or other social activities around the campfire during the summer months.
Mind you, just because it’s a tiny house, the only thing you skimp on is space. Every tiny house here has hot running water, electric heat, a flush toilet and hot shower. That’s all I need!
Hotel Vintage
I really enjoyed my stay in this spacious and luxurious Kimpton brand hotel. I’m not sure why they call it the Vintage, because the décor is chicly modern, from the invitingly modern multi-story lobby to the guest rooms. I enjoyed the mini-bar, which was surprisingly affordable! I’m not sure if this is true of a lot of their rooms, but mine had this interesting hidden skylight that let in natural light from the ceiling, it was quite cool!
The bed was fantastic, and my room included an adjacent elevated seating area accessed by two steps – which made the room seem a lot more spacious than it actually was. I also enjoyed the wall art – a circular wall hanging made of wine corks with an image of a lady burned into it.
Stay Pineapple at Hotel Rose
Another fun and funky hotel right along Portland’s downtown waterfront park. An inviting bar and lounge beckon you as you enter, and the décor is brightly colored – some may even say whimsical. Take the elevator to your room, and upon entering the sleek and stylish room, your bed will greet you with a seductive accent pillow that literally says “Sleep with Me.” This hotel would be perfect for that romantic rendezvous.
The StayPineapple boutique chain offers their “naked experience” with big fluffy towels (among the fluffiest I have experienced in a hotel!) and comfy robes. They also offer coffee, and treats of the pineapple variety in the lobby. Situated in the heart of downtown, great dining and shopping is all nearby. They also rent bikes so you can explore the area.
To put it simply, there is no excuse not to live the Portland dream at any one of the great hotels.
