Categories: Explore Oregon

The Jennings Hotel: A Superbly Stylish Passion Project

The Jennings Hotel is a superbly stylish passion project in the lively town of Joseph

written by Jen Stevenson

As the autumn chill sets Eastern Oregon’s bigleaf maples ablaze and the season’s first snows paint the almighty Wallowas winter white, roll your dusty wagon down the main street of Joseph, a wee but lively Wallowa County town that’s made a name for itself as a bona fide destination for adventurers both artistic and extreme—with the boutique hotel to match.

A superbly stylish passion project dreamed up by “accidental hotelier” Greg Hennes and brought to life by an ambitious Kickstarter campaign, this unlikely mecca of art, design and creative camaraderie sits on the top floor of Joseph’s Jennings Building, a two-story circa-1910 brick structure that could have been pulled straight from a spaghetti western. Inside, things get decidedly more modern—each room was designed by a different acclaimed artist, architect, or designer, and no two are the same. Some rooms have private bathrooms, other share, and everyone’s welcome in the Scandinavian-style cedar sauna, where piles of soft Turkish towels and detailed instructions on how to properly löyly await.

Across the hall, the communal kitchen and living room inspire conversation over a shared meal or bottle of wine as Cat Stevens plays on the turntable, while the floor-to-ceiling wall library sends Dostoevsky and Dahl-laden bookworms scurrying for a seat by the wood-fired stove. And after a night of deep, restful sleep only possible in a town with no stoplights and near-zero light interference, wake up, grab a cup of Stumptown coffee and something sweet from the Arrowhead Chocolates shop downstairs, then decide what the day’s adventures will hold—a 20-mile trail hike, a downtown walkabout or perhaps just breakfast and books in bed.

Each room at The Jennings Hotel was designed by a different artist or designer, like this room by Brendon Farrell.
Room 8, designed by Greg Hennes.
Room 6, designed by Shelter Collective.
Room 4, designed by Kate Sullivan.


None of the boutique hotel’s twelve rooms’ design and décor are alike, so check each listing closely to find your sleepaway soulmate—snuggle in a whitewashed fir and brick loft in Room 7, wake up to stunning views of the Wallowas in Room 3b, enjoy private access to the hotel’s mountain-facing balcony from Nordic-themed Room 2, and for those looking for the liberty of their own kitchen and bathroom, book bright and airy Room 6.


Design, architecture, and history buffs alike will appreciate the curation of each unique room in the 108-year-old building, one of which might sport a luxurious tufted blue velvet Rejuvenation sofa, another a weaving wall that guests are encouraged to embellish. Cook breakfast in the light-filled kitchen while plotting a trip to nearby Wallowa Lake, borrow a good read from the expansive library, or warm wintry bones in the cedar sauna, just the spot for a meet, greet, and sweat with a fascinating cross-section of guests from all over the world.


Cooking in couldn’t be easier in the hotel’s well-stocked communal kitchen, but there are plenty of dining options along Joseph’s cheerful bronze-statue-lined main street. Cozy up with a cappuccino at Red Horse Coffee Traders, savor sausage-stuffed Swedish pancakes at homey Old Town Cafe, raid the truffle case at Good Food Award-winning Arrowhead Chocolates, sample whiskey at Stein Distillery (call ahead to book a tour), share the pork banh mi and Thai iced tea cheesecake with your favorite four-legged friend at The Dog Spot, and slide into a booth for juicy Stangel Ranch bison burgers and pints of Cross-Eyed Cricket IPA at East Fork Brewery. End the day listening to live music with the locals at Embers Brew House, which claims the largest selection of microbrews in Eastern Oregon.


When planning your visit, check the course schedule at Prairie Mountain Folk School, a nonprofit dedicated to teaching and preserving heritage trades. Co-founded by Greg Hennes, the school holds classes and workshops covering everything from canning and spoon carving to timber cabin building and willow mat weaving; find detailed class descriptions and enroll at

100 N MAIN ST.

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