The Best Hotels in Oregon

It was touch-and-go at moments, but 2017’s wildfires spared the lodge at this iconic waterfall in the Columbia Gorge, 30 miles east of downtown Portland. The stone structure at the site of the 620-foot, two-step falls was built in 1925, ten years after Multnomah Falls Park was dedicated. It’s an easy, paved hike up to the Benson Footbridge, situated between the upper and lower falls. On weekends and in the summertime, traffic can be a bear, so plan accordingly, either by arriving early or by taking advantage of the Gorge Express bus service, which departs regularly from the Gateway Transit Center in Portland.

Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.

Situated on Northeast Portland’s Alberta Street, smack in the middle of the Alberta Arts District, Caravan is an unique alternative to the same old hotels or vacation rentals. The hotel is comprised of six tiny, individually styled houses for rent, from the cabin-like Skyline (made mostly from upcycled material) to the Amazing Mysterium (a vaguely steampunk affair modeled after a vardo gypsy wagon, with lovely additions such as stained-glass windows and lots of built-in shelving). In true Portland style, the houses are clustered together in a “pod,” similar to how many of the city’s famous food carts are arranged. In lieu of a lobby, there’s a central outdoor common area with a fire pit (s’more-making is encouraged, and supplies are provided). Note that live bands perform for guests and a limited number of community members on Wednesday evenings during the summer months, and the whole area gets busy on the first Thursday of every month, when Alberta Street transforms into a pedestrian-only night market-cum-street party that lasts well into the evening.

Rising from the ashes of the 60’s Red Lion Hotel is the east side’s latest entry into Portland’s hip hotel scene—the Eastlund. Cut from the same pedigree as the downtown Modera Hotel, the Eastlund is a welcome upgrade in the evolving convention center area. The fun starts in the bright, expansive lobby, where eye-catching art welcomes visitors. The staff is tuned to deliver exceptional customer service, and the vibe is genuine and unpretentious. Amenities include great food, local spirits, tech-savvy rooms, and super-fast Wi-Fi throughout the property.

The rooms and public spaces put art front and center, while the meeting areas are wired for productivity. Business and leisure travelers also benefit from attention to detail and a staff committed to getting it if it’s not already available. The efficient, comfort-forward rooms boast big flat-screens and colorful décor, and the river and city views from the upper levels are spectacular day and night. An easy MAX ride from the airport, The Eastlund is also delightfully located within walking distance of a variety of transportation, entertainment, meeting, and dining opportunities. With so many on-site amenities, however, you might just find yourself pleasantly planted during your Portland stay.

Most people recognize Eugene, Oregon as the home of the “Oregon Ducks” because of the sports programs at the University of Oregon. But Eugene is so much more. Take for instance the Inn at the 5th, a luxury boutique hotel built and owned by the Obie Company who developed the 5th Street Public Market next door. The hotel reminds me of the “Little Engine That Could” an endearing 1930’s children’s book teaching the value of hard work and optimism. And the Inn at 5th presents those core values to guests in a stylish and polished package.

Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland’s most iconic grande dames, and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines.

Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that.

Housed in a converted elementary school dating back to 1915, this sprawling hotel complex has long drawn out-of-towners and local Portlanders alike with its bars, restaurants, miniature movie theater, and even a heated soaking pool that’s open to the public for a small fee. While these amenities—along with the hotel’s sprawling school grounds and proximity to the popular Alberta Arts District—are enough to make it one of the most attractive spots to stay in town, its real cred shines through in the 57 guest rooms, many of which are actually converted classrooms (and still have some of the original scholastic features, such as chalkboards, integrated into the room design). Don’t leave without sampling some of the McMenamins signature brews in the Boiler Room Bar, housed in what was once the school’s boiler room.

Portland isn’t exactly the kind of city that’s known for being “fancy,” which was why it was so bold for the Starwood Luxury Collection to add a sleek 15th floor to the top of the iconic Meier & Frank department store building downtown—and turn the top nine floors into the swankiest hotel in town. Who would’ve thought that Louis XVI chairs, tufted white leather and teal velvet, crystal chandeliers, and ornate wallpaper would work so well in the city of plaid, beards, and twee bird patterns? In true Field of Dreams fashion, Starwood built it and the travelers came out of the woodwork, hungry for a luxury hotel that embodies the Rose City with everything from environmentally conscious practices and farm-to-table restaurants to an extensive art collection and rooftop honey bee colony. All that’s to say nothing of the private club-like Library, a collaboration with Portland icon Powell’s Books (the world’s largest bookstore) that allows hotel guests to borrow from a curated collection of 3,000 books during their stay. As it turns out, it’s not all that hard to dress Portland to the nines.

Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.

The Sunriver Resort is near Bend, Oregon, which is a rightfully famous, and incredibly beautiful, area for outdoor adventure. In the winter, there is skiing at nearby Mt. Bachelor (25 min away), but the summer has even more to do, including golfing, hiking, mountain bike riding, tennis, and of course, swimming in the resort’s amazing pool, which has a water slide, sand play area, hot tub, and amazing views of Mt. Bachelor and the golf course. The rooms are up to date and nicely appointed. The main lodge has a great bar area, a nice restaurant, and a large “back lawn” with live music and kid-friendly activities. Overall, a highly-recommended place for a family vacation.

Actually, the lobby of the Sapphire Hotel is as far as you’ll get when you visit these days. And for all intents and purposes, it’s far enough. The Sapphire maintains the edge its enjoyed since its inception in the early 1900s. Then a gathering place for the quirky and lightly mannered; cool before cool was cool, it now is the great-grandparent of PDX hip. The candlelit scene keeps the conversation low and the alcohol levels, therapeutic. With cocktails like: You’re Not My Real Dad, Retrosex, Winter Isn’t Coming and Floozie, what could possibly go wrong. The hotel rooms are long gone, but the kitchen still hangs around. The menu maintains a simplicity and charm of another era. An order of the salmon corn cakes with a Sapphire salad will easily sustain, but why stop there. Go for the fully-loaded Sapphire burger, have another pop and regroup for the ginger-vanilla bean creme brûlée. The best thing about the Sapphire is the hang time. It’s out on the bleeding edge of Hawthorne, so once you get out there, you’ll tend to want to linger. The atmosphere encourages it with a sharp wait staff supported by bartenders that roll the dice to delver concoctions you can’t get just anywhere. Happy hour tends to evolve into happy evening, even happy night. I’d say it was a gem, but that would be stating the obvious.