The Coolest Airbnbs In Oregon

Explore the rest of your home state with a more adventurous staycation

Honorable Mention: One of Tye Haus' A-Frames. (Bryan Daugherty)

Even as a born-and-bred Oregonian, I thought Bend was eastern Oregon for a long time. I thought Crater Lake was essentially next to Idaho, and that all I could look forward to at the coast was cheddar cheese samples and the Newport Aquarium.

With emerging neighborhoods to discover in the Portland area every few months, one can quickly grow oblivious to the vacation gems tucked beyond (or within) our modest metropolis. For those who are more familiar than foreign, the forests of your childhood will feel very different when waking up on the second story of an architecturally-complex A-frame cabin.

A famous river retreat designed by architect Willard K. Martin in unincorporated Clatsop County. (AirBnB)

A Writer's Paradise at Soapstone Woodland River Retreat

This whimsical cottage, located twelve miles east of Cannon Beach in the fringe of the Clatsop State Forest, features a "writing cube" on the third level, perched forty-feet above the main floor and aligned exactly north, south, east west. It has a built-in desk and large round windows on all four sides. Cheryl Strayed, author of "Wild," has stayed here, according to the host. Enjoyed twenty-two acres and  private riverside trails.

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Centrally located, just three blocks walking to SE Hawthorne and Division St. (AirBnB)

Magic Barn in Division Neighborhood

First built around 1936, this former sculpture studio has been restored by community artists with old growth barn wood, up-cycled furnishings, kitchen, claw foot bath, and a sculpture garden. Just a few blocks from some of our city's best bars, restaurants and shops on SE Hawthorne and Division. Get the 2-bed, 1-bath all to yourself for $81 a night.

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A mid-century A-frame with character. (AirBnB)

Retro-Modern Hood River Getaway 

Experience the best of all worlds in this stylish, well-appointed cabin just over a mile from downtown Hood River. The 2.5 acre property has views of Mt. Hood and Mt. Adams, near Post Canyon's world famous mountain biking spot, and features WiFi, a fireplace, and other modern amenities inside. With two bedrooms and one bathroom, you can have up to six guests at $220 a night.

(Airbnb)

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Staying longer than 2 nights at this farm/rental/vintage 1970 Airstream? You get a free bottle of wine. (Airbnb)

Rogue River Airstream Eco-Farmstay

Fancy cabins are cool, but you're leaving the city to experience something other than the ordinary. This vintage Airstream is completely off the power grid, with a compost-style toilet (though a hot shower & real toilet is on the premises, just a short walk away). Depending on the season, you can learn how to milk a goat, hike nearby trails, and borrow a mat from the owners for a mountaintop yoga session.

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Art and nature at its most rentable. (Airbnb)

Saul Zaik Treehouse

Located in the SW hills of Portland, this masterpiece is considered the "Coolest Treehouse in the World" by Condé Nast Traveler. The entire lower level is available to rent, with a bedroom with queen bed, private bath, and sitting room designed for lounging.

Adjacent garden at the Saul Zaik house. (Airbnb)

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Inside the SkyHaus (airbnb)

Honorable Mention: Sky Haus Cabin in Skykomish, WA

A cozy stay for five guests in this stocked Washington cabin located about 15 minutes from the slopes and some of the best hikes the PNW has to offer. The loft bedroom area has fresh linens on the beds and the hot tub outside the front door is always ready.

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