Having never visited Portland before, my first moments staring at Google Maps were a little overwhelming. When you start planning a trip to a new place, it can be really hard to get a firm grasp on where you should stay and why. Funnily enough, the more you read, the more things can become very confusing. It wasn’t until I actually got to Portland, stayed in a few different places and got a feel for the different areas that I began to really understand it properly and get a good grasp on the best places for visitors to stay. So, based on my experiences at three very different hotels in three very different parts of town, here’s my guide on where you should stay in Portland. Hopefully, it clears a few things up for you and helps you find the perfect spot for your travel needs!
Let’s get oriented!
First things first, here’s a map of Portland with all three spots marked by a star. They are Kimpton Hotel Monaco, McMenamins Crystal Hotel and Jupiter Hotel. This will serve as a nice little visual for you, helping you understand where each is located. In my opinion, most visitors will find everything they want to see, do and eat within the area of this map. Of course, if you have access to a car, you may find yourself exploring beyond Portland’s central areas. If you take a close look at the map below you’ll notice the central city areas are laid out in a grid format, making it easy to find your way around by foot or bicycle. Even if you don’t end up staying in one of the three hotels I’ve mentioned, you’ll have a bit more insight into which area is best suited to your needs.
Kimpton Hotel Monaco
Where: You’ll find the super stylish Kimpton Hotel Monaco located in Downtown Portland, right in the heart of the City Centre. For first-time visitors, this means the hotel is based in a really central location, making it very easy to find your way around town on foot or bicycle. It’s a nice easy stroll to the Portland Art Museum, down to the waterfront or up to the Pearl District. The hotel offers free bikes, which makes it easy to buzz across to East Portland or up to Arlington Heights, home of the must-see Japanese Garden and Zoo, as well as the beautiful Northwest District.
Being based Downtown, it is located close to many services for Portland’s significant homeless population. So just keep in mind you will see many people sleeping rough and hanging out in the area surrounding the hotel. This can also bring with it a few unsavoury sights and smells. I found it a little intimidating at first, only because it’s not something I’m used to, but that subsided as I adjusted to it and realised there was no threat to my safety. I don’t think the hotel should be punished for its location and don’t think it should deter people from staying here, it’s just something you need to know ahead of time so you know what to expect and don’t feel shocked when you arrive.
What: If you’re looking for a luxury stay with a modern edge, Kimpton Hotel Monaco is your pick. I stayed in a King Corner Room and found it to be bright, airy, very comfortable and spacious. I had plenty of room to spread out and make myself at home. I loved the big cosy bed, perfect for getting a great night’s sleep, as well as the bathroom, complete with huge mirror ideal for getting ready each morning. The hotel offers free wifi and it’s really good quality (yay!) as well as supplying funky bathrobes, lovely bath products and is pet-friendly too! I also loved the live music every evening and social hour, featuring local wines.
Who: I would recommend Kimpton Hotel Monaco to my parents or anyone looking for a luxury stay, like couples on holiday. The hotel has that really professional feel to it, where you just know they’ll take care of whatever you need and ensure your stay is seamless. The rooms are fantastic and the location is perfect for first-time visitors, especially. I would just remind anyone looking to stay in the Downtown area that Portland’s homeless population does tend to be more prominent here, so keep that in mind.
McMenamins Crystal Hotel
Where: You’ll find the McMenamins Crystal Hotel sitting rather elegantly and proudly on the edge of the Pearl District. Of all the places I stayed in Portland, the Crystal was my favourite in terms of location and unique experience. Even though it’s only a few blocks from Downtown, you’ll find the homeless population in this area is significantly less. In terms of sightseeing, you’ll find it easy to get around on foot or by bicycle. I ventured up to the Northwest District, explored the Pearl District and Downtown from here. I caught an Uber up to Arlington Heights, home to the Japanese Garden, Washington Park and Zoo, then walked back to the Crystal easily and safely.
What: If you’re looking for a unique hotel experience that really immerses you in Portland’s culture, the Crystal is perfect. The century-old, flatiron building has a fantastic historic feel to it, with each room individually decorated to reflect a song or performance at the neighbouring Crystal Ballroom over the past 100 years. The rooms here are small, offering only a bed, table and two chairs, basin and mirror… and I loved it! There was no tv or mini bar or any of that extra stuff you come to expect from cookie-cutter hotel rooms, this was a far more organic experience.
Rather than gutting the glorious hotel and replacing it with identical rooms, they’ve kept it as-is and, in doing so, retained a truly unique, old-world, historic experience you just can’t get anywhere else. The bathrooms are shared, which can put some people off, but I found them to always be beautifully clean and I never had to wait to use them or even ran into another person using them at the same time (there are 9 rooms with private bathrooms if you prefer). The hotel also provides free wi-fi, which is really good quality, so if you are the type who likes to watch TV to relax (me) be sure to BYO laptop or tablet.
Who: I would recommend McMenamins Crystal Hotel to couples, probably anyone from 18 through to 50 would love it. The hotel is in a fantastic location, I loved the entire Pearl District and all the great cafes, restaurants and shops in the surrounding area. I also loved how easy it was to get around and see, do and eat everything I wanted and there’s a WholeFoods across the street, which makes for a very convenient meal option. I would just say, noise from the surrounding streets can float up into the rooms but the hotel provides earplugs. Personally, I didn’t find the noise to be bothersome, it was kind of nice knowing the world was still out there, especially as I was travelling solo.
Where: You’ll find the Jupiter Hotel tucked, rather inconspicuously, among the streets of South East Portland. In comparison to the other side of town, I found this area to be a little more quiet, with a chilled-out, low-key vibe going on. Away from the busy streets of Downtown, SE Portland has a certain relaxed pace to it. Again, being away from Downtown, the homeless population here was noticeably smaller, though I was asked for money a few times.
I got the chance to experience SE Portland on a bicycle, thanks to the team at Cycle Portland, and loved riding down beautiful streets lined with American Elm Trees. I found this side of town required a little more planning, rather than dumb luck, to find the good spots. When you do find them, my goodness, they are well worth it! If you are planning on staying in SE Portland, I’d definitely recommend hiring a bicycle to get around, just to save your legs a little when venturing over to Downtown.
What: Jupiter Hotel offers a modern, boutique experience. I found my room to be a great space, offering plenty of space for one or two guests to spread out and get comfortable. The floating bed was really comfortable and I got a great night’s sleep each evening. The room itself provided a bright, hip interior. From what I could tell, it used to be a run of the mill motel but has been renovated. Personally, I really liked the new fitout! The bathroom, while compact, offered everything I needed and I found it to be lovely and clean. Free wifi was great quality, it was very spacious, well maintained, bright, welcoming and cosy, with plenty of fatnastic eateries and cafes located closeby.
Who: I would recommend the Jupiter Hotel to couples, again anyone from 18 through to 45 would be well-suited, particularly those who don’t really want to be ‘in the thick of it’ and are after a more chilled out stay. Think bicycle rides, local coffee shops, food trucks and craft breweries. Those with heavy luggage might like to request a room on the ground floor so they don’t have to carry bags up the stairs. I stayed on a Friday and Saturday – Friday was nice and quiet, Saturday there was a bit of bass pumping from Doug Fir, the on-site lounge and bar. The hotel provides earplugs and the noise didn’t bother me personally, but I think guests like my mum, for example, might find it bothersome.
Phoebe Lee is a travel writer and award-winning blogger with a love for storytelling. Phoebe creates practical, fun and engaging written content designed to inspire and energise travel-lovers and dreamers. Follow her and Matt’s adventures at home and around the world, right here on Little Grey Box and through Instagram, Facebook, and YouTube.