As far as origin stories go, the Jennings Hotel in Joseph has a good one. The two-story building went up in 1910 on a prominent corner of the Eastern Oregon town’s Main Street, constructed by a Norwegian bricklayer. The original project was helmed by a Mrs. Edith Jennings, who, per the Wallowa County Chieftain, intended it to have an “opera house” upstairs and “business room” on the lower story. At some point, the upper level was divided into rooms for a hotel or boarding house, while the lower level stuck to retail, hosting everything from bars to artisan provisions to home goods and even an undertaker in the ensuing decades.

The upstairs rooms became offices, then apartments, complete with dropped ceilings, textured drywall, and peel-and-stick vinyl floors. This was its state when Greg Hennes bought it eight years ago for $355,000. Hennes's goal was to extensively renovate, keeping the downstairs retail and converting the rest into a boutique hotel and artists’ residency. As was well-covered in the press, the renovations were led by a successful Kickstarter campaign, which promised everything from a several nights stay to a leather key fob, and raised a total of $107,070, garnering a catchy tag line in the process as “the hotel that Kickstarter built.”

Now, Hennes is selling the whole package, which includes the 3,000 square feet of street-level commercial space, a separate adjoining tax lot to the north, and the 14-room boutique hotel, complete with all its branding, operations, fixtures, and furniture.

For the hotel’s design, Hennes took an interesting approach: a different designer friend tackled each room, which fit well with the piecemeal tactic of remodeling a few rooms at a time. Thus, there’s a lot of talent on display here, both national and local to the PNW, from Ben Klebba of Phloem Studio (Rooms 3a and 3b), to Portland architect and product designer Brendon Farrell (Room 7), and Kate Sullivan, founder of Portland Flea (Room 4).

As might be expected, the room designs range. They include pared back treatments that focus on a good mix of furniture and accessories, many Oregon made—all the better to show off the newly raised ceilings and exposed brick walls. (Such is why the hotel has been used for more than a few catalog shoots.)

Other rooms are like a lesson in small space design, like Room 1’s bed nook and wall-mounted desk. Still others play with materials to novel effect, like Room 5’s coved plaster and bespoke furnishings, all done by Portland studio Linden, Brown Architecture, and Room 11’s cocoon of wood around the bed, finished by Hennes.

The common spaces, of course, are equally considered, with a kitchen-and-library furnished in Phloem Studio cabinetry. And even the sauna gets in on the game, thanks to a redwood bench fashioned by Eugene designer Tom Bonamici.

Listing Fast Facts 

• Address: 100 N Main St, Joseph, Oregon 97846
• Size:  10,200 square feet, 14 guest rooms, two land parcels for a total of 12,217 square feet
• List Date:  10/30/2023
• List Price:  $3,200,000
• Listing Agent:  N/A

Melissa Dalton is a freelance writer who has focused on Pacific Northwest design and lifestyle since 2008. She is based in Portland, Oregon. Contact Dalton here. 

Editor’s Note: Portland Monthly’s “Property Watch” column takes a weekly look at an interesting home in Portland’s real estate market (with periodic ventures to the burbs and points beyond, for good measure). Got a home you think would work for this column? Get in touch at [email protected].