A Step-by-Step Guide to Email Campaigns for Existing Customers

You got the booking. Now what?

Most property managers stop at the confirmation email. Maybe they send check-in instructions. But the guest journey doesn’t end at checkout—it’s where the real opportunity begins.

The guests who’ve already stayed with you are your most valuable marketing channel. They know your property. They had a good experience. They’re 5-7x more likely to book again than a cold lead.

This guide walks through the email campaigns that turn one-time guests into repeat bookers—step by step, from booking confirmation to the anniversary reminder that brings them back next year.

The post-booking guest journey

Once someone books, there are 9 key moments where the right email makes a difference:

During the booking: Booking confirmation, Trip extensions (upsell)

Before the stay: Pre-trip preparation, Check-in day

After the stay: Post-trip review request, Flash rebook, Convert OTA to direct

Long-term retention: Stay again (anniversary), Guest winback

Each email serves a specific purpose. Let’s walk through them in order.

Step 1: Booking confirmation

When it sends: 5 minutes after booking

Purpose: Confirm the details and set expectations.

Example:

Subject: You’re confirmed at Mountain View Lodge

Hi Sarah,

You’re all set. Mountain View Lodge is yours from March 15, 2024 through March 18, 2024.

We’ll send check-in details 2 days before you arrive. Until then, if you need anything, just reply.

What to include: Property name and dates, check-in/check-out times, number of nights and guests, brief property description, what happens next, how to reach you.

Why it matters: This is transactional, not promotional—but it’s your first impression after they commit. Clear details and a warm tone set the stage for everything that follows.

Step 2: Trip extensions

When it sends: 2 days after booking confirmation

Purpose: Offer additional nights if you have availability before or after their stay.

Example:

Subject: 2 more nights available at Mountain View Lodge

Hi Sarah,

Mountain View Lodge has 2 nights open after your stay.

Current booking: March 15–18 | 3 nights | $1,247

With extension: March 15–20 | 5 nights | $2,045

Want them? Reply and I’ll add them to your reservation.

What to include: How many nights are available and when, side-by-side comparison of current vs. extended booking, clear pricing, easy action.

Why it works: You’re not asking them to make another booking decision—you’re offering to make their existing trip better. This increases average booking value by 12-20% when availability exists.

Step 3: Pre-trip preparation

When it sends: 3 days before check-in, 9am in property timezone

Purpose: Give them everything they need for a smooth arrival.

What to include: Access instructions (codes, parking, entry process), amenities highlights, location context, how to reach you with questions.

Why it matters: This reduces “how do I get in?” messages on arrival day. It also builds anticipation—remind them of the hot tub, the views, the trails. Guests who are excited before they arrive have better stays.

Step 4: Check-in day

When it sends: 8am on check-in day

Purpose: Final confirmation that everything’s ready.

Example:

Subject: Mountain View Lodge is ready

Hi Sarah,

You’re all set. Check-in opens at 4:00 PM.

WiFi: MountainView_5G | BlueRidge2024!

Need something? Text (828) 555-0192 or just reply here.

What to include: Check-in time, access instructions (repeat them—people don’t save emails), WiFi network and password, your phone number for day-of questions.

Step 5: Post-trip review request

When it sends: 24 hours after checkout

Purpose: Collect reviews while the experience is fresh.

Example:

Subject: How was Mountain View Lodge?

Hi Sarah,

You just checked out. How was it?

If you’ve got 2 minutes, leave a review. It helps other guests decide, and it helps me keep the place up to standard.

Want to come back? Just reply—I’ll make it easy.

Why it matters: Reviews build social proof. The timing matters—24 hours is soon enough that they remember details but late enough that they’re home and settled.

Step 6: Flash rebook

When it sends: 10 hours after checkout

Purpose: Capture rebookings while they’re still glowing.

Example:

Subject: Same weekend next year?

Hi Sarah,

You just checked out from Mountain View Lodge.

Want the same weekend next year? Reserve it now at today’s price.

Offer good until Friday, March 22 at 11:00 AM.

Why it works: You’re asking when they’re happiest—right after a great stay. The price lock creates urgency. This fills your calendar a full year in advance with guests who already love your property.

Step 7: Convert OTA to direct

When it sends: 48 hours after checkout (for OTA bookings only)

Purpose: Turn Airbnb/VRBO guests into direct bookers.

Example:

Subject: You booked Mountain View Lodge through Airbnb

Hi Sarah,

When you book direct, you skip the platform fees. That’s usually 15-20% back in your pocket.

Why it works: Most guests have no idea how much goes to Airbnb. You’re educating them on a better option for next time. Over time, this shifts a meaningful percentage of OTA guests to direct channels.

Step 8: Stay again (anniversary)

When it sends: 11 months after their original stay

Purpose: Prompt a repeat booking at the same time next year.

Nostalgia is a powerful booking driver. You’re not selling—you’re reminding them of a trip they loved. The 11-month timing gives them a month to plan before the anniversary date.

Step 9: Guest winback

When it sends: 9+ months after checkout (if they haven’t rebooked)

Purpose: Re-engage lapsed guests with an incentive.

A 15% discount code with an expiration date gives them a reason to book now instead of “someday.” Only send to guests who haven’t rebooked—don’t offer a discount to someone who already has an upcoming reservation.

What makes this system work

They’re triggered, not scheduled. Each email sends based on a specific event—booking confirmed, checkout completed, 11 months passed. You’re not blasting everyone with the same message.

They’re personal. “Questions? Just reply.” “Want them? Reply and I’ll add them.” This isn’t a corporate newsletter.

They follow the journey. Confirmation → extension → preparation → check-in → review → rebook → anniversary. Each email meets the guest where they are.

They respect timing. Pre-trip sends 3 days out at 9am. Flash rebook sends 10 hours after checkout. The timing is as important as the content.

Setting this up

You can build these campaigns yourself. The logic isn’t complicated. But building the templates, connecting your booking system, testing the triggers, and maintaining everything takes weeks of setup work.

That’s why we built it into Wander Sites. When you launch a direct booking site with Wander Sites, all 9 of these campaigns come pre-built. Booking confirmations send automatically. Check-in instructions go out on time. Anniversary emails trigger when they should.

You don’t configure anything. You just turn it on.

The same lifecycle email nurturing behind $55M+ in bookings—now powering your direct booking site.

Start here

If you’re setting this up yourself, prioritize in this order:

1. Booking confirmation + check-in day — Essential guest experience

2. Post-trip review request — Build social proof

3. Flash rebook — Capture rebookings while intent is high

4. Pre-trip preparation — Reduce day-of questions

5. Everything else — Layer in as you have time

The guests who’ve already booked with you are your best customers. Treat them that way, and they’ll come back.

Want all 9 campaigns running automatically? Wander Sites includes lifecycle email nurturing out of the box—no setup required. Get started free at wander.com/sites