Hey, it's Anastasia.

In today’s issue:

• Yurts in Nature – A peaceful stay surrounded by nature.
• FIFA’s Impact Report – A look at how FIFA is influencing different regions.
• Hotels Launch in ChatGPT – The first direct booking app for hotels appears inside ChatGPT.
• Montreal STR Ban – Seasonal short-term rental restrictions could cost millions in tourism revenue.
• Deals on the Market – 35 keys in New York, 11 cabins in Minnesota.
• Bookings During Low Season – Step-by-step guide.

and more...

🌿 Unique Stays

Yurts in nature​

(there is a nice video on their website if you scroll a bit down)

Art in nature​

📰 Industry News

Check out this report on FIFA’s impact on different areas​

The first direct booking app for hotels launches in ChatGPT​​

​Montréal seasonal short-term rental ban risks millions in tourism revenue

💼 Deals

11 cabins in Minnesota​

35 keys in New York​

Underground house in Virginia​

Movie ranch in New Mexico​

700 acres in Tennessee​

Disclaimer: The content of this newsletter, including any mentions of tools, features, updates, news, deals, or personal experiences shared, is provided solely for informational and entertainment purposes. It does not constitute investment, financial, legal, professional, or any other form of advice, and should not be relied upon as such. Always conduct your own research and consult qualified professionals before making any decisions related to property management, software tools, business operations, or investments.

How to get bookings during low season?

Let’s do it step by step, and I will give a couple of examples from what we are doing.

Step 1. Understanding your seasons

First, you want to know exactly when your high, low, and shoulder seasons are.

Then check and adjust them based on new data that might appear due to new events.

For example, we consider June a low season in Austin, but this year is different due to FIFA.

If you ran your numbers a year ago, rerun them.

One tool I like using for this is PriceLabs Market Dashboard.

For example, in our case we consider our low season to be:

• January
• February
• June
• July
• August

August can sometimes move into shoulder season territory, but for simplicity let’s assume it is low season.

Since June turned into a high season month this year, we remove it. That leaves us with:

• January
• February
• July
• August

Step 2. Do we rent it as a short term rental or as a mid term rental?

To make that decision we need comps and a simple Excel file with calculations.

To estimate short term rental performance:

• Use the PriceLabs dashboard to understand ADR.
• Apply filters for your property type.
• Manually review comparable listings.

Next, estimate occupancy.

Then calculate approximate monthly revenue using this formula:

ADR × Occupancy × Number of days in the month

This gives you an approximate monthly revenue.

Create three scenarios:

• Worst case
• Mid case
• Best case

Finding mid term rental comps

To estimate mid term revenue, check:

• Zillow
• Apartments.com
• Similar furnished rental platforms

Set filters for:

• Your location
• Similar property type
• Furnished rentals

Then collect a range of comparable monthly rents.

Make sure the properties are truly comparable to yours.

At this point your Excel sheet should show monthly revenue estimates side by side.

Comparing operating costs

Now estimate expenses.

For mid term rentals:

• Assume about one cleaning per month.

Even when we host guests for two months, we require a monthly cleaning. This helps preserve the homes in better condition.

For short term rentals:

• You might get 4-6 reservations
• Average stay might be 2 days
• This means higher turnover costs

After estimating expenses, calculate the final profit for each option.

Return on headache

My husband Rod likes to add another metric to this equation.

He calls it Return on headache.

Mid term guests are often significantly easier to manage compared to 4-6 separate reservations per month.

Even if calculations show slightly higher revenue for short term guests during low season, we often lean toward mid term rentals because of this metric.

One more important factor

Low prices can attract bad actors.

This happened to us before.

99.9% of our guests are wonderful people who love staying with us and we love hosting them.

But less than 1% of guests have caused significant damage or had bad intent when booking.

Even though these situations are rare, they leave a lasting impression and affect our days.

One way to avoid offering the lowest prices during the lowest months and attracting bad actors is offering mid term stays instead.

Step 3. Setting up pricing for mid term stays

If you use a combination like we do:

• PriceLabs
• Hostaway (PMS)

You can create a seasonal pricing profile for low season.

Then apply:

• Base price
• Floor price
• Ceiling price

In your PMS you can also add:

• Weekly discounts
• Monthly discounts

One important rule when testing pricing strategies:

Start with higher pricing first.

This helps confirm everything is working correctly before lowering prices.

I have seen hosts accidentally publish incorrect pricing and get instantly booked at unintended rates.

Once pricing looks correct:

• Compare your listing to similar listings
• Check how your discounts look
• Adjust if needed

Then move to the next step.

Step 4. Finding the guests

The beauty of mid term stays is that you do not need many guests.

Often you only need:

• 1 guest
• or 2 guests

Sometimes a guest may even book two months consecutively.

Why people book mid term stays

Common reasons include:

• Corporate work assignments
• Visiting family and friends
• Transitioning between homes
• Remote workers exploring new cities

Where we find guests

In our case we have been collecting guest emails since we started hosting.

More importantly, we have built relationships with some guests.

Sometimes when we want to fill the low season we reach out individually to guests who stayed with us before.

Some stayed:

• once
• twice
• even three times

If you can fill 1-3 mid term spots with returning guests, it becomes a win-win.

They get:

• the first invitation
• direct booking
• a place they already know and trust

Filling the remaining spots

After that you may only need one or two more bookings.

You can:

• Send an email to your guest list with a special offer
• Capture guests through Airbnb or Vrbo
• Create additional listings on Zillow or similar platforms

That's all for today.

Till next week, dear readers.

p.s. We often drive to Dallas to visit family, and every time we make the trip we stop at Buc-ee’s.

There are two Buc-ee’s between Austin and Dallas, and every single time we stop it’s a great experience. It’s clean, spacious, and there are so many options. The quality of the food and products is noticeably better than most places you can stop along the road.

And there are always people there, no matter the time of day or day of the week. I honestly don’t remember the last time we stopped anywhere else on that route.

It has even become a highlight of our road trip. We actually look forward to it, and it makes the whole drive more enjoyable.

Yesterday, as we were coming back from Dallas, I saw a new gas station opening not far from one of the Buc-ee’s. It looked modern and nicely designed, but my first thought was: how are they going to compete with Buc-ee’s?

In a sea of uninspiring gas stations and convenience stores, Buc-ee’s managed to be something completely different.