Digs Co.: Chelsea Dunckley on Building Vacation Rentals in Roslyn and Cle Elum

Chelsea Dunckley went from a degree in Spanish and European studies to commercial real estate, a tech startup, and a basement she and her husband Luke dug out of a crawl space one five gallon bucket at a time. Then they built a house in Roslyn and turned it into Digs Co., a vacation rental business in the Cle Elum and Roslyn area. Scott talks with Chelsea about how it started, what guests actually ask for, and where she goes for coffee.

The application that beat the vote

Chelsea and Luke built their first rental, Roslyn Digs, from the ground up in downtown Roslyn. Luke’s dad is a builder, and the couple holds a general contractor license. Partway through the build, the city put a moratorium on new vacation rental licenses while it decided whether to ban them on their street.

Chelsea read through the city’s own documents and found that the moratorium had lapsed for about 48 hours. She ran to City Hall with her youngest son in a stroller and slid the application in at about 5:45 PM, just as the meeting to vote on it began. Roslyn Digs has been licensed ever since. And the name? Roslyn is an old coal mining town.

Hospitality, not property management

Chelsea spent years managing shopping centers and calls that work thankless. Short term rentals feel different to her because the guest is a family on a two night trip, not a business on a five year lease. Her advice to anyone thinking about getting in: there is nothing passive about it. Put the guest first and sweat the details. Four to six pillows on a king bed, spare charging cords, good coffee, and board games, which guests use far more than the books.

When this conversation was recorded in spring 2022, Digs Co. ran six houses of its own, including Sun Country Digs and a 1960s A frame on Lake Cle Elum, plus six homes it hosts for other owners. Chelsea and Luke also consult on the numbers, branding and interior design for people starting out.

Chelsea’s picks around Cle Elum and Roslyn

• Coffee: Pioneer Coffee Roasting Co. in Cle Elum. Digs Co. buys its beans wholesale there for the houses.
• More coffee: Basecamp Books and Bites.
• Golf: Sun Country Golf Course, which she calls less daunting than Suncadia and a lot cheaper.
• Local partner: Owens Meats, one of the local businesses Digs Co. works with.

See three of the Digs Co. cabins in our earlier piece, Exploring Digs Co. Cabins Near Cle Elum, and plan the rest of the trip with our Cle Elum guide.

Find Digs Co.

Book a stay or ask about hosting on the Digs Co. website (one G in Digs), or follow along on Instagram at @thedigs.co.

Remember, there’s always more to explore.