Explore, Then Sleep: Where to Stay in Oregon



Initially, when I imagined spending the night in Oregon, I pictured it being somewhat of an adventure — hiking to a secluded beach, setting up camp and falling asleep listening to the roaring waves pound against the shoreline after having one too many Rogue beers.

But on this particular journey, I had the pleasure of calling it a night in a few of the best hotels in the Beaver State, after checking out some of its seven wonders.

Oregon has plenty of terrific places to stay. Just ask anyone.

Whether it’s comfort and style at the most exquisite hotels or boutiques, cozy, romantic bed and breakfasts, great seaside inns, quaint cottages, family-oriented vacation rentals, or simply kicking back solo and relaxing with a cocktail and warm fireplace, Oregon offers some of the finest lodging on the West Coast.

From organizing activities and tours, excellent turndown service, delicious food, spa treatments suited for royalty and entertainment, once you check in at one of the Pacific Northwest’s best, you’ll be checking out for the weekend (or month). It’s your choice.

If you’re wondering where to stay in Oregon during your next vacation or business layover, below are three really fabulous recommendations.

Jupiter Hotel

The location and aesthetics of this place are hard to beat.

With close proximity to some of the most amazing restaurants, bars, shopping and entertainment in Portland, as well as ultra-modern minimalist guest rooms, this mid-century motor inn is super rad.

It features 80 non-smoking rooms, all boasting fantastic murals of relaxing forest scenes to John Lennon and Marilyn Monroe, and one large suite with a bar for hosting a party for up to 25 guests. Each room comes equipped with a chalkboard door (perfect for any memories or thoughts you want to scribble down or inspirational messages you want to leave behind), a few condoms to ensure you’re practicing safe sex, eco-friendly Natura bath products, and maybe even one of your favorite books! My room just so happened to have one of mine, The Four Agreements!

This boutique hotel in the heart of the City of Roses is truly a happening place.

Not to mention, just steps from the entrance of your room is the Doug Fir Lounge, an amazing bar, restaurant and music venue that serves up some amazing Northwest cuisine, like one hell of a Dungeness Crab Burger (complete with lemon aioli, braised winter greens and a toasted brioche bun). The drinks aren’t too shabby, either. If you drop in for happy hour, you’re sure to make some new friends.

You’ll want to try one of the local brews or the Wood Fir’d Manhattan — the Woodford Reserve Bourbon is quite tasty!

Although during my stay there weren’t any musical acts performing, the Doug Fir is one of the hottest live music venues in the US, and is known to host some serious talent. In 2013, Rolling Stone Magazine dubbed this place one of the top 20 “Best Clubs in America."

Other amenities at this property include, ZipCar rentals, free wifi throughout the property, city bikes for rent, computer access, and great front desk concierge service.

The Cannery Pier Hotel

Only in Astoria will you find such a quaint seaside retreat.

Located on the ocean roads west of Portland, this hotel is built on the site of the former Union Fish Cannery, 600 feet into the Columbia River. And when they say this place is on the water, they mean it.

While there’s plenty to see and do in Astoria, if you book a room at this hotel, you might not venture too far from your room.

After checking-in, I found myself wishing I was on a romantic getaway and not traveling solo, because the cozy en-suite fireplace and inviting bathtub (I could have sat in that bathtub and watched ships go by on the river for hours) were enough to encourage me to hang the “Do Not Disturb” sign on the door and disappear from public view for an unknown amount of time. That is, after indulging in a massage at the full-service day spa, enjoying complimentary wine and lox in the lobby and trying the finest restaurants and cocktails the region has to offer.

Each room is the epitome of charm and comfort, offering hardwood floors, gigantic bathrooms with large, walk-in showers, a fireplace and a private balcony, where you can watch the massive ships pass by on the Columbia River under the Astoria-Megler Bridge with a pair of binoculars.

You can even request a schedule from the front desk, so you can see when the ships are coming in and where they are traveling from. The staff are also great at recommending the best spots in town to do some shopping, catch the best happy hours, fresh seafood and legitimate landmarks worth visiting.

Other amenities at this property include bike rentals, sunset cruises aboard a 65-foot yacht, a personal chauffeur who can ride you around town in an antique 1939 Buick or 1946 Cadillac, continental breakfast every morning (you get to make your own waffles!) and freshly baked cookies each evening.

Planning an escape to Astoria? You’ll want to do yourself a favor and pamper yourself by staying here. After just one night, you will most likely never stay anywhere else in Astoria. Sure, it’s no longer the best kept secret in the Pacific Northwest, but it’s still worth a visit, or two, or five.

The Benson

You already know that Oregon’s lure is world-renowned, but so are its hotels.

And since we’re suckers for history, The Benson Hotel in Portland has to be the next hotel on our short list.

This hotel’s rich architectural appeal, old world charm, superior hospitality and classic décor make it the pinnacle of elegance and style in this extraordinary city.

Located on Southwest Broadway and Oak Street, The Benson is truly a rare gem.

The architecture whispers tales of a bygone era – Austrian crystal chandeliers, imported, now extinct walnut pillars, coffered ceilings and a marble staircase.

In the lobby you’ll find the Palm Court (where the people watching is excellent), the hotel’s famed restaurant and lounge. Though small, the bar is exceptional, especially when Jonah Kobayashi, a Hawaiian native, is behind it and jazz music plays in the corner.

The Palm Court may be known for its black-tie service, but it has always been known as a jazz house and a place for good vibes.

It’s the perfect place to drop in for a drink if you happen to be wandering around town and find yourself thirsty, or craving a light meal.

Kobayashi describes the feeling of Portland as one that brings people coming back for more, and explains why they are usually booking a luxurious room at The Benson.

“It’s young and vibrant,” he says. “It’s a comfortable enough city that you want to stay, but one that also doesn’t make you so complacent. Portland is the perfect location for The Benson, especially considering the old world charm the city provides. The Benson is the place to stay for top-class, presidential service. You know, the kind of service folks were used to getting back in the day.”

For an islander to feel comfortable in the Northwest, how can you argue?

He recommended I try the Duck Confit (crispy duck with potatoes and pickled onions) to go with my ice-cold beer and Jameson neat. The duck was outstanding to say the least. I’d go back just for that.

Jazz filled the air in The Palm Court, and the singer reminded me of something I told myself I would never forget, “Today is all we have. It is the first day of the rest of your life.” Those are probably the words that should be carved into every bar top.

Feel like enjoying an award-winning steak in a private dining room instead of eating near the lobby? You’ll want to check out El Gaucho, located adjacent to the hotel. Here you can enjoy world-class wine lists, live music and delectable dishes in an intimate setting.

For those inclined to engage in some old-fashioned tourism, the hotel is a stone’s throw from the some of the finest dining, shopping and entertainment in Portland.

When you decide you want to put the outside world on hold, when you feel like stepping back in time, step into The Benson.

Last month, the hotel celebrated its 100th birthday.


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