The CheckIn

Issue 004 · Tuesday, May 19, 2026

Booking goes alt, Vrbo rewrites Premier Host, and the bath sheet your guests are quietly judging you for.

Plus: the morning-of-arrival text that drops check-in fire drills from 1-in-3 to 1-in-12.

The Check-In · May 19, 2026

Booking goes alt, Vrbo rewrites Premier Host, and the bath sheet your guests are quietly judging you for.

The 5 Headlines

  • Booking.com's Q1 2026 results say alternative accommodations now make up 38% of the company's total room nights, with the property count hitting 8.8M (+9% YoY) and gross bookings up 15%. The world's largest accommodations OTA is no longer a hotel-first business.
  • Vrbo's Premier Host program just got rewritten: badges now attach to individual listings, not host accounts, and require 99% acceptance, 0% cancellation, and a >9.2 rating per property. AI review summaries, a property Q&A bot, and dynamic-highlight tagging are live on every listing.
  • The 35-by-70-inch bath sheet (not the standard 27-by-54-inch bath towel) is the cheapest perceived-luxury upgrade most STR operators skip. Hotel-grade options from Brooklinen, Onsen, and Riley run $40 to $80 per piece, and the first guest who unfolds one in your unit will text someone about it.
  • Mid-term rental booking windows are tightening hard: per Furnished Finder, 40% of monthly renters now secure housing within two weeks of move-in, while 28+ night stays have jumped from 20M nights in 2019 to 46M nights at the end of 2025. If your reply time is over 48 hours, you're not in the running.
  • AirDNA's midyear 2026 read: 2025 finished with US STR demand growth at 5.7% and listings at 4.6%, occupancy slightly up. For 2026 the forecast calls for stability rather than swing: occupancy easing ~1%, ADR up 1.5%, supply +4.6%, with the World Cup pumping above-trend RevPAR in the nine US host metros.

Pro Tip: the morning-of-arrival ETA text

It takes 30 seconds and saves you an hour. The morning of arrival, send your guest one short text: "Hi! Excited to host you today, what's your ETA looking like?" You'll get a reply 9 out of 10 times.

Why this works: the guest running early reveals it, so you don't get a 1pm knock when check-in is 4pm. The guest running late tells you, so you don't sit by the phone wondering if they got lost. And the guest who has no idea remembers there's a real human on the other end, which makes them text the moment something goes sideways at the door.

It also creates the first one-on-one warm contact of the stay. The 4-star review that flips to 5 stars is almost always preceded by a guest who felt seen before they walked in.

We've watched check-in fire drills drop from 1-in-3 to 1-in-12 with this single text. Cost: 30 seconds. Frequency: every guest, every arrival, day-of.

Dream Weaving: the kitchen-counter chalkboard

There's a small object that's earned its place on every kitchen counter we run: a slate-and-wood chalkboard, maybe six by eight inches, that simply reads "Welcome, [first name]."

It costs $12 on Amazon. It takes the cleaner 20 seconds to update between guests. And it does something the welcome basket cannot: it makes the guest stop. They walk in, they see their name on a chalkboard in a stranger's house, and for a half-second they feel known.

Half of them photograph it. A quarter of those share it. (Try searching #welcomechalkboard on Instagram if you're curious.) The Spanish family staying with us this week will text it to grandma in Sevilla. The couple traveling for a wedding will use it as a backdrop for the morning-after coffee shot.

Cost: $12 plus chalk. Effort: 20 seconds per turn. It's the smallest thing that signals we knew you were coming.

Press Play: a Whistler operator's actual playbook

A short video, podcast episode, or audiobook chapter for the commute, kitchen, or hot tub.

Thanks For Visiting · Podcast · ~50 min listen

How Laura Wegner Built a High-Performing STR Brand in Whistler

Annette Grant and Sarah Karakaian sit down with Laura Wegner, a Whistler-based operator who's quietly built one of British Columbia's most distinctive STR brands. They walk through her actual playbook on data, design, and strategic pricing, the kind of operator detail that usually sits behind a paywall. Made for a Saturday morning coffee.

A Towne Motel guest room with a Jesse Link polar-bear-sailboat painting on the sage-green accent wall

Spotlight

The Towne Motel revamp, Camden, Maine

The Towne Motel · 17 rooms · Camden, Maine · five minutes from the harbor.

Vintage motor-lodge bones, freshly renovated interiors. Sixteen standard rooms plus one pet-friendly studio, a short walk to Camden Harbor, the schooners, and the village core. Beautyrest mattresses, organic bath products, and the small bed-and-breakfast touches that make a motel stay feel like the right kind of small hotel. Book direct at camdenmotel.com.

The Towne is operated by Ohana Vacations, the team behind The Check-In. If you own a small motel or boutique inn that needs operators, or you're an owner thinking about handing the keys to a team that lives this work, we're actively looking to manage and buy more. Reach out: billyo@ohanavacations.com.

Sources

Credit where it's due, and a doorway in if you want to dive deeper on any of the above.

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