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How to get high $$$ bookings starting tomorrow

How to get high $$$ bookings starting tomorrow

Scott Quesnell
August 14, 2025

If you want more large group bookings, this is for you.

Groups are not going to book using a calendar widget.

Instead, these large ticket purchases require human interaction.

Which makes sense.

Most group bookings start at $1,000 per night. I have never spent more than $1k online without talking to a person.

Have you?

In 2025 and 2026, if your goal is to book more:

Company retreats
Wedding parties
Roundabout Appreciation Society get togethers.

You must follow 2 steps. These are achievable for anyone:

1 ) Create The Offer

First, people must know you offer group bookings.

Don't overthink this. A small section on your home page with a group bookings menu item is perfect.

Then, we have to create the offer page by answering the 5 questions guests ask:

Who
What
Where
Why
How

a) Who

Who is your stay perfect for hosting? Is it:

Small teams (5-10 people)
Large weddings (50+ people)
Tailgate parties (go Packers!)

Whatever the answer, say it. Examples:

"Group bookings for up to 50 people. Perfect for weddings, small teams and large families."

b) What

What's in it for the group? For the most part, this can be the same pitch you would give to a single unit booking.

Give a list of the amenities
Paint the site with photos
Good to go

Note: If you offer large group discounts, mention that here too.

c) Where

Tell people where you are. Make your address public or at least mention the nearby town.

We like to give distances from major locations. Example:

1 hr north from Boston
3 hrs east from Nashville
Downtown Tulsa. 15 minutes from the river
Over the river and through the woods (to grandmothers house we go)

d) Why

This is the most important point. I promise, there are only 1-3 reasons why people are choosing you over anyone else.

Don't spend a bunch of time thinking about those reasons.

Instead, read reviews. People will mention:

The views
Proximity to world class hiking
Common social areas

People will tell you why you're the perfect place for a large group getaway. Go with that.

e) How

There is one final step to creating your offer. Tell people how to book.

99% of people will not charge $1,000+/night to their credit card after reading your offer.

They want to talk to you. So let them.

The call to action on your offer page should be something like:

Get started
Start now
Create your package

Not "Book now."

Then give them two ways to contact you.

Phone number
Contact form

2 ) Get Leads

The best way to book group bookings is by driving phone calls or form fill-outs.

Aka, leads.

I love getting leads through Meta ads (shocker).

Why?

They can be really inexpensive. Like $20-$30 per lead.

How to run ads for this is super simple:

Create 3-5 videos that highlight your stay + premium amenities.
Place text on those videos that is the answer to your "who" question (Group bookings for up to 50 people. Perfect for weddings, small teams and large families).
Run a Meta Leads campaign.
Target every city within a 2-3 hr drive.

That's it!