Nook & Nestle | STR Co-Host & Operations Manager

We're Nook & Nestle Stays, a short-term rental management operation based in Chicago with over $1 million in gross earnings managed, across 20+ active listings, 1,165+ guest reviews and an average 4.7 rating. You got into short-term rentals to generate income and build financial freedom, not to spend your nights answering guest messages and your weekends coordinating cleaners. If the business has started feeling more like a second job than an asset, that's exactly what we fix. We partner with property owners nationwide who are tired of leaving money on the table, especially heading into peak season when every unoptimized night is revenue you never get back. The difference between a well-run listing and a poorly run one isn't luck, it's systems, pricing, and execution. What sets us apart is that we're active operators, not consultants who've read about it. We manage real listings in real markets using professional dynamic pricing tools, proven guest communication systems, and a vetted vendor network. You get the same infrastructure we use on our own portfolio, applied directly to yours. We handle everything remotely and professionally so you can finally step back, collect your returns, and let the asset work for you the way it was supposed to from the start. We're currently onboarding our first 5 Thumbtack clients at a reduced introductory rate with all onboarding fees waived. Once those spots are filled the rates go back to standard pricing. If you're heading into peak season with an underperforming listing, now is the right time to make a move. Let's jump on a quick call today and just talk through your listing honestly — what's working, what isn't, and exactly what it would take to get it fully optimized.