The CheckIn

The Source · Killington, the Beast of the East

What I Wish I Knew on Day One

Jenna's raw and real tips for a smooth Killington launch. The mountain forgives a lot, but it doesn't forgive bad operations.

Jenna Spencer

Jenna says

Raw and real. The fastest way to a smooth Killington launch is to skip the avoidable scars.

  1. 01.

    Register before you do anything else.

    Every winter I watch new owners close on a Killington condo in October, photograph it, list it, and then realize they didn't register with the town before they took bookings. Killington's STR registration runs annually November 1 to October 31. You can't legally accept a guest under 30 nights until the registration is in hand. Apply at killington.munirevs.com on the day you close. If you have an existing unit and you've been lazy about renewal, today is the day. Not Monday.

  2. 02.

    Your insurance is wrong. Almost certainly.

    A standard homeowner's policy does not cover short-term rentals. Full stop. Vermont specifically: if a guest falls on your icy front steps in February and breaks a hip, your homeowner's carrier will deny the claim the second they discover it was a paid stay. Get a real STR policy, Proper, Steadily, CBIZ Vacation Rental, your pick, and confirm in writing that the carrier knows the address operates as a short-term rental. Vermont winters are brutal on stairs, gutters, and roofs. Underinsured operators here go bankrupt one slip-and-fall at a time.

  3. 03.

    Read the HOA / condo association docs before you close. All of them.

    Killington's resort-area condos vary wildly in their STR rules. Mountain Green is openly STR-friendly. Some other complexes have written 30-night minimums into their bylaws, or have outright banned anything under 6 months. The town's STR registration does NOT override your association's rules. If your realtor doesn't pull the full bylaws + amendments for you in writing before closing, get a different realtor. I've watched five- and six-figure annual income become zero because of a clause on page 47.

  4. 04.

    Plowing is a license issue. Treat it that way.

    A guest who can't get into your driveway at 2am during a Tuesday blizzard does two things: writes a 1-star review, and calls the town. The town pays attention to 'this STR is causing problems' complaints. So your plowing is part of your operations, not an afterthought. Get a plow contract before snow flies, October at the latest, with a contractor whose phone you can actually reach. Pay them well. Confirm they'll come for every event of 2+ inches, not when they get to you. Build a backup plow into the contract or in a side text thread with a second contractor. Even with a plow contract, keep a snow shovel and a bag of salt on the porch for guest use. Bonus points for a windshield scraper in the entryway. Storms hit between plow visits, and a guest who can dig themselves out of the last six inches loves you for it.

  5. 05.

    The Killington Cup weekend is not a normal weekend.

    The FIS Audi World Cup at Killington (women's GS + slalom, Thanksgiving weekend in years it runs) brings international ski media, athlete families, tour-stop staff, and a brutally tight inventory window. ADR runs 2× to 3× the rest of winter. The catch: it's the SAME WEEKEND as Thanksgiving, so half the resort's regular family customers are coming anyway. Price the World Cup weekend separately the moment the FIS calendar drops in spring. Pre-bake it into PriceLabs / Wheelhouse. Don't leave the rate at 'auto.'

  6. 06.

    Summer is real now. Don't underwrite it as a void.

    Killington's $60M investment in mountain biking, golf, and adventure infrastructure has changed the math. Revenue still peaks in February, but August and October now produce more than half what the mid-winter weeks do, AND the operating costs of a property are lower in summer (no plowing, no propane spikes, less wear). If your underwriting assumes ski + nothing else, you're modeling 2017 numbers. Pull AirDNA on summer/foliage Killington and rebuild the spreadsheet.

  7. 07.

    Foliage is the highest-margin two weeks of the year.

    Late September into mid-October is the highest-margin window in Vermont. ADR runs nearly winter-peak, operating costs run summer-low, occupancy approaches 75%+. International leaf-peepers book 90+ days out. Price aggressively into the first week of October, the foliage window shifts each year with the weather, but the booking window doesn't. Watch the New England Foliage Network reports starting Labor Day; they're useful for fine-tuning.

  8. 08.

    Smart locks save you in mud season.

    Killington in April is mud, fog, and 38-degree rain. Guests arriving in that weather do not want to hunt for a lockbox. Get a smart lock on day one, Schlage Encode, Yale Assure, August, RemoteLock, whatever fits your door. Auto-generate codes per booking, auto-expire at checkout. The lock pays for itself in the first quarter from killing phone-tag at check-in alone, and in winter it eliminates the lost-key-in-snow disaster that happens to every operator who skips it.

  9. 09.

    Cell signal is not a given. Plan for the moment it isn't.

    Vermont coverage has gotten better, especially on AT&T, but you're still only at roughly 50% statewide carrier overlap. At some point a guest will fumble with the smart lock at 9pm, in the dark, in the rain. Are you 100% confident their phone will pull enough signal to call you? Two moves that quietly save the night. Run one wifi network with no password. Name it something obvious like Welcome-NoPassword so a guest standing on your porch can hop on without a code. Tape your direct cell number to the back of the lockbox, the inside of the smart-lock housing, or the front-door frame so they can text from any random Vermonter's phone if they have to. The worst version of this story is the guest who gets back in the car and drives twenty minutes down the road just to make a call. They don't come back happy.

  10. 10.

    How mountain logistics impact your reviews.

    Everything that happens on the mountain impacts you, even when your property isn't slope-side. Guests understand you don't control the weather. But a bad ski day feels vastly different than a rainy beach day for two reasons. High expectations. Guests aren't tolerating the weather, they're chasing it. They came for the snow. The human element. When a lift closes for wind or icing, guests read it as a resort-management problem, not an act of nature. That frustration frequently rolls back into host reviews. Pro tip. Drop the link for Killington's official mountain text alerts directly into your pre-arrival email. By setting expectations early you protect the guest's experience: if a lift is delayed, they find out from the couch instead of standing at the base in 12°F. You turn a mountain frustration into a hospitality win, and that's what saves your 5-star rating.

  11. 11.

    Pick a PMS on day one. Even with one door.

    If you're juggling Airbnb + Vrbo + Booking.com from each platform's native dashboard, you will triple-book a peak ski weekend within your first year. Pick a property management system, Hostaway, Hospitable, OwnerRez, Guesty, and run everything through it. The subscription is real money. The alternative is operationally catastrophic, especially over Christmas / MLK / Presidents' weeks when one missed sync can cost $2,500.

  12. 12.

    Build a maintenance bench BEFORE you need it.

    On a Sunday morning in February, when the water heater fails at -8°F and your guests are checking out at 11am with a new family checking in at 4pm, you do not want to be calling around for help. Build the bench in October. A plumber. A handyman. A propane company. An HVAC tech. A locksmith. Pay each one for one preventive visit before the season starts, just to introduce the property. When you call them in a real emergency, you're not a stranger.

  13. 13.

    The cleaner makes or breaks you. Doubly so in winter.

    Killington runs same-day turns through ski season — checkout at 10am, check-in at 4pm, with snowmelt on every hardwood floor and ski boots dripping in the entryway. A great cleaning crew running a tight winter turn is non-negotiable. Pay them well. Pay them on time. Build redundancy: have a backup crew on standby. The day your primary cleaner's kid gets the flu at 11am for a 3pm check-in, you'll need that second number. The crews under STR Housekeeping below exist for this reason.

  14. 14.

    Plan for the bad review now. Before you get one.

    Not 'maybe.' Will. Probably inside the first twenty stays. The wrong response is to argue, plead, or demand a takedown. The right response is two short sentences: acknowledge specifically what the guest raised, state exactly what you did to fix it. Calm. Brief. Public. Then move on. Future guests are reading your response more carefully than they're reading the review.

  15. 15.

    The mountain is a small town. Behave like a neighbor.

    Killington has maybe 700 year-round residents. The plow guy, the propane driver, the cleaner, the maintenance pro, the building inspector, the realtor who sold you the condo, they all know each other. They talk. Treat every person you work with the way you'd want to be treated, pay invoices fast, return texts inside an hour, show up when you say you will. The mountain rewards operators who behave like neighbors and quietly punishes the ones who don't. (You'll see the difference within your first off-season.)

Got a tip we missed?

If you've been hosting in Killington for a while and there's a mistake you'd save a new operator from, send it. We'll add it.

jenna@ohanavacations.com

Jenna Spencer

About the curator

Jenna Spencer

General Manager · Ohana Vacations Vermont

Vermont hospitality is rooted in experience: mountain mornings, muddy trails, ski weekends, and the kind of places people return to year after year. Jenna leads Ohana Vacations in Vermont, where she works closely with homeowners, guests, and local teams to create stays that feel both elevated and deeply connected to the Green Mountains.

jenna@ohanavacations.com

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