The CheckIn

Issue 006 · Tuesday, June 16, 2026

Airbnb softens the refund, summer books early, and Dolly opens a hotel.

Plus: the ten-minute calendar pass that recovers three or four dead nights a month.

The Check-In · June 16, 2026

Airbnb softens the refund, summer books early, and Dolly opens a hotel.

The 5 Headlines

  • Airbnb is piloting an Extended Cancellation Option: guests pay a small fee at checkout for the right to cancel for a full refund up to 24 hours before check-in. Here's the part that matters for you — you still get paid per your existing policy, Airbnb covers the difference, and the canceled dates reopen instantly. It's live on Moderate, Limited, Firm, and Strict listings, and you can switch it off anytime.
  • HITEC 2026 took over San Antonio this week (June 15-18), pulling nearly 6,000 pros and 370+ exhibitors, and the launches skewed hard toward AI and payments: Folio debuted what it calls the industry's first fully-embedded expense-management system, Samsung rolled out a hospitality version of its Frame art-TV, and roommaster showed a unified front-desk-to-revenue AI stack with 24/7 voice booking.
  • AirDNA's latest read has US summer bookings pacing well ahead of last year: June up 15.2%, July up 17.1%, and September already 24.2% higher year-over-year as travelers book earlier and stretch trips past Labor Day. Jackson Hole leads the summer pack at 45.5% occupancy.
  • Glendale, Wisconsin passed a new STR ordinance Monday after a shooting at an unlicensed rental: bookings under seven nights are now banned, every property needs a 24/7 in-town manager, and a health-department license is required. Local operators are worried it could price them out — one more Midwest town to keep an eye on.
  • Dolly Parton's SongTeller Hotel opens in downtown Nashville this month: 245 rooms behind a guitar-shaped entryway, two live-music venues (Parton's Live and Jolene's), and a 20,000-square-foot museum of her costumes and career — the largest Dolly exhibition ever assembled. Rates start around $400 a night, and it's already taking reservations.

Pro Tip: fill the orphan night before the calendar locks

With summer demand pacing double digits ahead, the money you're most likely to leave on the table isn't your nightly rate — it's the orphan night. Open your calendar and look for the one- and two-night gaps stranded between two longer bookings. If your minimum stay is three nights, those nights are unbookable, and they'll sit empty while the rest of your summer fills up around them.

Spend ten minutes Monday morning on this: find every gap of one or two nights in the next 90 days, and drop the minimum-stay rule on those exact dates to match the size of the gap. Then nudge the price up 10-15%, because a traveler hunting for a hard-to-find single night will gladly pay a little extra to land it.

One pass through the calendar can recover three or four otherwise-dead nights a month. At a $250 nightly rate, that's a four-figure summer you'd have quietly given away. Set a recurring Monday reminder and it turns into muscle memory.

Dream Weaving: the sound of the place

Sight and taste get all the welcome-gesture love: the chalkboard with the name, the basket of local snacks. Sound is the sense almost nobody touches, and it's the one that fills a room the second guests walk in.

Leave a small Bluetooth speaker on the counter with a handwritten card: Press play — this one's ours. The card carries a QR code to a short playlist you've built — fifteen or twenty songs by artists from your town or region, plus a couple of tracks that just sound like summer where you are.

It costs you one afternoon to make and zero dollars to reuse for every guest after. But the moment someone taps it and the kitchen fills with a local band they've never heard, you've done the thing a hotel chain can't: you've made the place sound like somewhere, not anywhere. Someone will Shazam a song. Someone will save the playlist and play it back home in February, and think of your house.

Press Play: the channel nobody can re-price on you

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

Hospitable Hosts · Podcast · ~40 min watch

6 Tips to Help You Grow Direct to Be 65% of Your Bookings

The same week Vrbo begins piloting paid "sponsored" placement and Airbnb keeps reworking the rules around your refunds, it's worth remembering the one channel nobody can quietly re-price on you: your own. Mark Simpson of Boostly makes the case for getting past 50% direct, then walks through how — know exactly who your guest is, build a recognizable brand of similar properties, become the go-to name in your niche, and put a real tech stack behind the scenes.

Not a brand-new release, but an evergreen one worth a re-listen any week the OTAs remind you whose house it really is.

Spotlight

Ohana is looking for more small inns

With Dolly opening 245 rooms downtown and a fresh wave of boutique openings this summer, here's our standing note at the bottom of the page: Ohana Vacations, the team behind The Check-In, runs small motels and boutique inns the way we'd want our own family's place run — and we're actively looking to manage or buy more.

If you own a small motor lodge or boutique inn that could use real operators, or you're an owner thinking about handing over the keys, we'd love to talk. Reach out anytime: billyo@ohanavacations.com.

Sources

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

Want the next one in your inbox?

Five headlines, one pro tip, dream-weaving, and a press-play pick. ~5-minute read. Free.

Free. Unsubscribe anytime.

← All issues