Write Emails for Bookings Using ChatGPT

Email lists are very powerful if you use them. Yet, most rental operators don't.

Here's why I love email marketing:

• Most people check two communication channels daily. Email and text

• No one doom scrolls their inbox

• Every element can be clickable

If email is something you want to do but can't get the momentum to start, this is for you.

Today, I'm going to give you a ChatGPT prompt that writes emails for you.

Note: Articles where I give away prompts are my highest rated. If you agree, rate this article "so good!" below. These take a little longer to make but if you love em, I want to keep making them.

How it works

This prompt will NOT give you a fun little newsletter with pretty pictures and stuff.

Expect your email to look like this:

• Focused on one subject matter

• 500 words max

• With a clear call to action

• Conversational and easy to read

• Optimized for transactions

Speaking of subject matters, I told ChatGPT to let you pick from three options:

1. Best dates to book

2. Things to do

3. Upcoming deals or promotions

These topics are what perform best for us so I thought you may want to start with your best foot forward.

Let's see. I'm trying to think if there's anything else I should mention about this.

Not really.

I guess, have fun! I mean you're literally about to have a robot write an email for you that may make you money.

If that doesn't blow your mind, I'm not sure what will.

Let's dive in. Beep-bop-boop.

Write Emails for Bookings Using ChatGPT

Use this prompt to write transactional emails for your list. Fill in the blank to match your unique situation:

You are an experienced short-term rental owner writing directly to past guests and interested subscribers.

Your goal is to write one polished, high-conversion email that encourages guests to book a stay now.

Writing Rules (Do Not Break These)

- Writing level: simple, clear, conversational
- Tone: owner-to-guest, warm and personal 
- No marketing jargon 
- No exclamation points 
- Focus on one subject only 

Email Topic (Choose ONE) 

- Best dates to book 
- Things to do 
- Upcoming deals or promotions 

Inputs (User Must Fill These In) 

Property location: 
[TOWN, STATE, REGION]

Email topic summary (1 sentence):
[WHY ARE YOU REACHING OUT?]

Available dates to promote: [LIST OF SPECIFIC OPEN DATES] 

Primary booking incentive: [ADD INCENTIVE]

Local specifics (REQUIRED): 

For each available date, include 1–2 specific, place-based experiences that make this stay feel unique to this location. 

Avoid generic ideas like “relax” or “explore.” 

Be concrete and visual. 

Booking CTA: [Exact wording for the next step] 

Email Framework (Follow Exactly) 

Headline: 
Write a short, curiosity-driven headline that hints at a specific moment, season, or feeling tied to the stay. 

Opening + Reason for Reaching Out:
One short paragraph explaining why you’re emailing, written like a real person who owns the property. 

Make it clear these dates are limited and you wanted the reader to have first access. 

Image Placeholder:
Insert this line exactly where a photo would naturally fit: {Place image here} 

Core Promotion / Benefit:
Anchor the email around one clear emotional reason to book (cozy winter reset, quiet family time, seasonal moment, etc.). 

Then: 

List the available dates 

Under each date, include 1–2 highly specific, local experiences 

Naturally tie the incentive into the story as a thank-you for booking early 

Use short paragraphs or light spacing 

Soft Urgency 

Gently remind the reader why timing matters: 

- limited winter availability 
- seasonal moments that won’t repeat 
- incentive deadline 
- No pressure language 

Clear Call to Action:

End with one simple, direct next step. 

Make it obvious what to do and why doing it now makes sense

Information you need to fill out:

Email topic: [CHOOSE ONE]

Property location [TOWN, STATE, REGION]

Email topic summary: [WHY ARE YOU REACHING OUT?]

Available dates: [LIST OF SPECIFIC OPEN DATES]

Primary booking incentive: [ADD INCENTIVE]

Booking CTA: [EXACT WORDING FOR NEXT STEP]

This is what I got:

I recorded a 10 minute video walking through this. Click here to view it.

Warning: Ai does a very good job at completing 80% of a task

The other 20% is room for you to:

• Add your creative touch

• Call out your ideal audience

• Focus on creating the best email you possibly can

I hope our little Ai friend gave you a promo you can use.

Next step: Even if they aren't perfect, send the emails. Your list wants to hear from you (that's why they signed up in the first place).

That's all for today. I'll see you in the next article.

P.S. Writing this from the Boston Harbor. I bought my buddy and I remote control boats for Christmas. Captain hats will be next.

This was a strategic purchase to get us out of the house because it’s easy to stay inside all winter. Plus, it’s hard to have a bad day if it ends playing boats at sunset.

Before you go

I spend about 10 hours writing this newsletter each week. The rest of my time is spent running Lodge Social.

Our marketing team will help you get more guests to like, share and book.

Work with me and my team here.

Links you might like:

1. Here’s my full demo on the above prompt (YouTube)

2. How to spot a good Airbnb investment at a glance (AirDNA)

3. Wander just released a direct booking website builder (Wander)

4. Marketing metrics that matter (The Lodge Social)