4* Hotel Rose - Staypineapple

The Hoxton suits Old Town rather beautifully: a historic building, moody interiors, local art and enough going on downstairs that you could accidentally spend half the evening in the hotel. There are 119 rooms with walnut panelling, mid-century touches and locally curated artwork, ranging from compact “Shoebox” options to much roomier categories. Upstairs, Tope is the real crowd-pleaser – a rooftop taqueria serving tacos and cocktails with city views – while the ground-floor and basement spaces keep things lively later on. The Old Town location is particularly useful for LGBTQ visitors because Stag, Silverado, CC Slaughters and Darcelle XV are all clustered around this part of town. Powell’s, the Pearl and waterfront are also within easy reach. GayMapper tip: Start with sunset drinks and tacos at Tope, then head out into Old Town – this is one of the easiest Portland hotels for turning dinner into a proper night out.

Vance is short for “advance”, which tells you quite a lot about the mood here: modern, creative and aimed at people who would rather have clever design than faux historic grandeur. Hotel Vance, Portland, a Tribute Portfolio Hotel sits in the Cultural District near Portland State University and the South Park Blocks. The rooms are contemporary and unfussy, with Vance + Vine Kitchen downstairs for Pacific Northwest-inspired comfort food and a Starbucks in the lobby for caffeine emergencies. There’s a 24-hour gym, good work spaces and – increasingly unusual in this segment – no destination fee. The Portland Art Museum and theatres are nearby, while the streetcar and MAX make the rest of the city easy. This is more about cultural Downtown than nightlife outside the door. GayMapper tip: A particularly good fit if you want smart modern design and central convenience without paying an extra daily fee for facilities you may never use.

There’s a completely different pace down by the Willamette. RiverPlace Hotel sits right beside the waterfront path and marina, making it feel almost resort-like even though Downtown begins only a few blocks away. The 85 rooms and suites range from straightforward guestrooms to larger cottages with fireplaces, full kitchens and washers and dryers. PUBLIC bikes are available for exploring the riverfront, yoga mats sit in every room and guests get morning coffee followed by a hosted evening social hour. RiverPlace Kitchen + Bar keeps things suitably relaxed with waterfront dining and seasonal American food. This is the Portland choice for couples who want peaceful river walks rather than nightlife immediately outside. The annual Pride waterfront festivities also happen virtually on the doorstep. GayMapper tip: Book a river-view room or cottage if the budget allows – the water is the whole reason this location feels different from Portland’s other downtown hotels.

Bright colours, pineapple motifs and a serious disregard for beige make Hotel Rose feel cheerfully at home in Portland. It sits directly opposite Tom McCall Waterfront Park, so riverside walks and Saturday Market mornings are almost too easy. Staypineapple’s signature extras are part of the fun: ridiculously comfortable double-duvet beds, complimentary welcome drink, afternoon pineapple treats and bikes for exploring the city. Bottle + Kitchen handles seasonal food and cocktails downstairs, while the rooms have everything needed for a comfortable downtown base without trying to become precious about it. The MAX runs nearby and Downtown is outside the door, so getting between the Pearl, Old Town and Portland’s scattered LGBTQ venues is straightforward. GayMapper tip: Take one of the Pineapple Bikes out along the river – preferably before sampling Portland’s breweries rather than afterwards.

The Mark Spencer Hotel has been part of Portland since 1907, but the experience today is less grand old hotel and more comfortable independent base with some surprisingly useful extras. It sits between Downtown and the Pearl, with Powell’s Books practically around the corner. Rooms have local art and polished modern finishes, while many of the larger categories include actual kitchens – ideal when you’re staying more than a couple of nights. There’s a fitness centre, guest laundry and a daily complimentary wine reception with Pacific Northwest wines and snacks. Breakfast can even be ordered to your room from neighbouring Cheryl’s on 12th. Restaurants, shopping and public transport surround you, while Old Town’s LGBTQ bars are easily reachable when you fancy a night out. GayMapper tip: Look at the kitchen-equipped rooms if you’re staying longer – having somewhere to make breakfast or reheat Portland leftovers is genuinely useful.

The Duniway feels like Hilton decided to loosen its tie for the weekend. Named after Oregon suffragist Abigail Scott Duniway, the hotel has a bolder, more individual look than the typical big-brand downtown stay. Rooms come with huge 65-inch TVs and espresso machines, while the heated indoor pool and fitness centre give you something useful to come back to when Portland’s weather does what Portland weather sometimes does. Mayrose is now the hotel’s restaurant and bar, replacing the older Jackrabbit setup you may still see mentioned elsewhere. Pioneer Courthouse Square, the Portland Art Museum and MAX light rail are all right nearby, making this particularly easy without a car. Old Town and Portland’s LGBTQ nightlife are also perfectly manageable on foot or a quick ride away. GayMapper tip: A good compromise if you like boutique styling but still appreciate the predictability and facilities of a larger Hilton.