Winter can be your most profitable season—or your most stressful. The difference comes down to preparation. Whether you're hosting at a ski resort (like Wintergreen, here in Central Virginia), managing a rural mountain retreat, or running an urban rental that sees occasional snow, having the right systems in place means the difference between five-star reviews and emergency maintenance calls at 2 AM.

Sandwich nights are the single-night stays wedged between longer bookings. They're the orphan nights that sit there on your calendar, mocking you, costing you money while you pretend they'll magically fill themselves.

They won't.

Cotton sheets are fine. They're perfectly adequate. They're what everyone expects, which is precisely the problem.

If you're running a higher-end short-term rental—something marketed as a boutique experience, a design-forward space, an escape from the ordinary—you need bedding that signals you've thought about more than just thread count and Amazon Prime delivery times.

You need linen.

I'm about to tell you how to make your Airbnb's outdoor space actually worth the "outdoor seating area" checkbox you're ticking in your listing.

Furniture with character makes small spaces memorable.

The truth is, guests remember spaces that make them feel something. Outdoors is where the magic happens— people actually sit outside and breathe when they are away from home. Outside is where they drink their morning coffee and text their friends "omg this place." That's your five-star review, sitting there under that string of lights you're about to hang.

So, you’ve fallen in love with Charlottesville — the brick sidewalks, the vineyards, the energy of the University, the mountain views — and you’re thinking, “Hey, I’ll buy a cute little house and rent it on Airbnb!”

Well… not so fast.

Charlottesville loves its visitors, but when it comes to short-term rentals, the city keeps things pretty tight. In fact, you can’t legally run a stand-alone Airbnb here — meaning you can’t rent out a property you don’t live in.

Let’s break down why that is (and why it’s not as bad as it sounds).

Airbnb announced they were going to prevent hosts from asking for certain tasks prior to check-out, like vacuuming, doing laundry, and stripping the beds. They call these “unreasonable.” I've never asked a guest to vacuum or do the laundry (though I have asked them to start a load of towels), but stripping the beds is a task that I would encourage EVERY GUEST who stays at an Airbnb to do. Here is why:

Cleaning short term rentals shouldn’t be “hidden” work. Let’s foreground its value rather than try to hide it.

Oh, potential Airbnb guest and/or stockholder, fret not. Cleaning fees are your friend. Allow me to explain.

THE best part of Airbnb, in my experience, is that the platform allows hosts to host in way that feels comfortable, safe, and worthwhile to them. Cleaning fees are one tool hosts (like me) use to make our space available to more people.

Photos say volumes about your short term rental space— they are the MOST important reason guests cite for booking a particular space.

Airbnb Cleaning fees are a powerful tools for hosts, but cleaning fees also matter politically.

Can you have an Airbnb in Albemarle county, Virginia? You can, but its pretty regulated. In Albemarle County, a “homestay” is basically a short-term rental — you’re renting out part or all of your home for fewer than 30 consecutive days.

You must live in the home (as your primary residence) to use it as a homestay.

Thinking about hosting your place for a few nights in Charlottesville (go ‘Hoos!)? Before you hit “List Now”, it’s worth knowing how the rules dance in this historic city. The good news: it’s totally doable — just funneled through some steps so things stay smooth for you, your neighbors and the City.In Charlottesville, the term you’ll run into a lot is “homestay”: a place rented for fewer than 30 days at a time.

Thinking about turning your home into a charming short-term rental in Albemarle County? Great idea — visitors love the mountain views, wineries, and easy access to Charlottesville. But before you hand over the keys, there’s a little paperwork to tackle first.

Here’s your easy, step-by-step guide to getting legal, complete with direct links to the forms you’ll need.

If you’ve ever dreamed of buying a little bungalow in Charlottesville and turning it into a full-time Airbnb, you’re not alone. Unfortunately, Charlottesville’s zoning and homestay rules don’t allow stand-alone short-term rentals — at least, not in most residential areas. Here’s why.