We’ll start with The Society Hotel; it’s perhaps the most
“Portland” of the hotels in our list on two counts. Firstly, it
blurs the line between poshtel (a posh hostel), hotel and rental
apartment in a progressive way that’s just so typical of the city.
Secondly, it’s housed in one of the city’s oldest buildings (it was
originally founded in 1881 as a mariner’s apartment complex) and is
speckled with artfully distressed antiques and 19th-century spoils
to prove it.

While the original Jupiter hotel has garnered a reputation as
the city’s go-to spot for thrill-seeking 20-somethings, Jupiter
NEXT is its more grown-up sister property – a six-floor, modernist
pad with more of a cocktail than tequila-chaser vibe inside. That
isn’t to say it’s dull. Jupiter NEXT treats guests to views out
over LoBu (that’s Lower Burnside, it’s A Thing) – one of Portland’s
less tourist-trodden but most lively neighbourhoods.

This riverside mansion is right in the heart of the city, though
you’d never guess from looking out over the grassy Tom McCall
Waterfront Park. If you grimace at the prospect of organised fun,
perhaps look elsewhere. Expect to be invited to yoga classes,
farmer’s markets and spots of fly fishing. The staff here even
invite guests to mingle over craft-beer tastings in the evenings –
this is Portland, after all.

If you weren’t already up to speed, “tiny house hotels” are
happening – thanks in part to this place in Portland’s bohemian
Alberta Arts District. This cluster of whimsically decorated
caravans started a nationwide trend for self-contained,
eco-friendly huts which are filled with all the amenities of a
house (albeit on a much smaller scale). They’re impressive
exercises in economising on space but maybe a little intense for
the claustrophobic…

Rock up to the graffiti-splattered streets of any formerly
up-and-coming destination and you’ll find an Ace Hotel. We’re not
complaining. True to form, Ace’s Portland outpost is peppered with
retro-style fittings – a photo booth in the lobby, record players
in each bedroom – and we’re head-over-heels in love with the
building’s art-deco shell which dates back to 1912.

Design-savvy types should book a room at this 20s-style hotel
when they’re in town. You won’t find any hipsters kicking back in
the cool cloisters of this industrial yet luxurious pad in central
Stumptown. Inside, it’s a glossy prism of dark wood, reclaimed
tiles and polished brass illuminated by hand-blown glass fixtures.
Grab a table at its Bullard restaurant, where chef Doug Adams has
combined the recipes of his Texan roots with the bounty of the
Pacific Northwest.

Okay, The Hoxton might be a chain hotel so to speak, but it’s a
good one. Tucked just outside the red gates of Old Town Chinatown,
its Portland outpost is a multicultural mishmash, decorated with
European mid-century furniture and grounded by a Mexican restaurant
which serves possibly the best tacos in the city. Don’t just take
our word for it…

Lovers of all things Scandi will be smitten with the
design-driven hostel located in gritty East Burnside. There’s a
smorgasbord of pickled fish, cheese and capers for breakfast,
Jolaglogg (an Icelandic mulled wine) stocked in the bar and a sauna
(of course) in the basement. Upstairs, 14 private rooms and 15
shared rooms play with Portland’s creative energy: headboards are
refashioned from old fireplaces and the eccentric wallpaper is
hand-drawn by a local artist.