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How to Attract Repeat Bookings with Automated Emails – Part 2

Written by: Beth Hamilton, Product & Marketing Manager

Now that you’ve read all about “How to Attract Repeat Guests”, let’s talk about how you increase repeat bookings using automated emails. In this blog, I am going suggest that you work on sending 6 key marketing emails to your guests and I’ll explain why they are important.

Let’s start by discussing why marketing emails are important:

In hospitality, as of April 2021, the average open rate for emails was 18.35% – higher than the overall average for all industries combined. Below we’ve included a summary of a few other industries that are interesting – including the industries with the highest and lowest open rates:

Reaching 18.35% of your clientele to gain feedback and provide a compelling offer for repeat business is significant and will have an impact on your bottom line. In fact, many of our customers have reported growth rates of repeat business by more than 30% as a result of sending emails to their guests post departure; the key being that they were successful in acquiring guest email addresses. If that doesn’t convince you, here are a few interesting statistics related to email marketing communication:

  1. Email campaigns generate $38 for every $1 spent.
  2. 73% of millennials prefer communications from businesses to come via email.
  3. 90% of content marketers say email engagement is the top metric they track to measure content performance.
  4. 49.5% of marketers planned on raising their email marketing budget in 2019, so companies who don’t at least match the efforts of their competitors could risk falling behind.

This all sounds appealing but I know what you’re thinking: this is great, but how do I make it easy? Through technology and automation; that’s how.

Collecting email addresses

An email campaign is dead in the water if you do not have guest email addresses to send them to. There are a few ways that you can encourage guests to provide you with their email addresses:

  1. Building wide guest WiFi: our customers have found significant success in collecting guest email addresses by requiring it as an authentication method for WiFi access. Using passwords is out of date, challenging for guests, and increases guest support calls. Using a simple name and email address authentication allows you to collect data, reiterate terms of use on the property, gauge how many individuals are in the party, and allows you to communicate with everyone that’s staying. If you want additional verification, connect your WiFi platform to your PMS and authenticate using last name and room number like most hotel brands do. 

  2. Collection at time of check-in: if you still have a front desk agent or even a kiosk for the guest to check in with, including some verbiage will assist with email collection. A common phrase I’ve heard in the past is, “In case you lose or forget anything in the unit, can we please have an email address to contact you in order to return the item?” This shows that you’re considerate and gets you what you’re after. 
  3. An app: Apps seem to be a trend that isn’t going away, although this isn’t my preferred method for data collection. Requiring an email address to utilize the app certainly makes sense, although you’re taking a chance that guests are really interested in what your app has to offer.

Whatever your tactic, make sure you follow GDPR, CASL, or any other pertinent data collection/emailing legislation in your area. It is also important that your emails include an “opt-out” or “unsubscribe” feature otherwise you run the risk of irritating your guests.

Two other technologies to make marketing emails easy:

  1. Automated email platform: there are many platforms to choose from, with MailChimp and Constant Contact and Campaign Monitor being the market leaders. These allow you to create email templates, create lists, and automate emails. It’s important to identify if your PMS and/or guest WiFi platforms can connect into these automated email platforms to make your email journey easier.
  2. Consider using technologies that help you find local content and events that you can include in your emails. Something like BuzzSumo or GuestViewGuide will help you find relevant content that applies to your guests based on location and industry.

Now that you know the relevant technologies to help you gain access to guest email addresses and how to cultivate and send your content, what are the emails that you should be sending? Well here they are:

What emails should be sent?

  1. Booking confirmation email. Of course this only works if you have the booker details, meaning that they are likely a repeat direct guest and they did not book through an OTA. The most important part of this email is to keep it brief and all about their itinerary. The only time I would recommend including area details is when the arrival window is less than 7 days out – in which case it may be tough to also send them a pre-arrival email.

  2. Pre-arrival email. Here is your chance to upsell the guest to local attractions and include details important to their arrival (i.e., Is there construction in the area? Is parking available? Are there public health restrictions? etc). What’s important about this email is that it should be sent outside the cancellation period; IE if they must cancel within 7 days, send it 10 days out. This gives them the chance to cancel without penalty, saving your team from dealing with an unhappy guest.

  3. Welcome email. This should be sent upon arrival to the property, particularly when they sign onto the WiFi using their email address. This is a chance to again, present any terms and conditions and  get any service issues out of the way, include support contact details, and highlight key features of the unit/property. Including area attractions, local restaurants, and places to purchase groceries also goes a long way to making a guest feel at home. 

  4. Post-stay email. This email should go 24-48hours post departure and is focused on collecting guest feedback in the form of a survey. In part 1 of this blog series, we included a few tips on how to encourage guest responses. Two important details are: keep the email and the survey brief, and only include the request for the survey in this email so as to not overwhelm the guest. Feedback is important for growth and improvement and the best way to do that is through an online system.

  5. Reminder email. This email should be sent ≈30 days post-departure and focuses on encouraging repeat business. There is very little “official” research to say whether repeat guest discounts work – but they are certainly worth a try to then monitor for results. Similarly, repeat guests are more apt to spend more money with your brand – so why not consider an upselling option (i.e., better suite, a package, or local add-ons), to increase your incremental revenue.

  6. Change of travel season email. The date range on this email is really customizable based on your area and local attractions or your high/low seasons, and it is very important to remind your guest of their amazing stay with you & encourage them to plan a return trip. Highlighting local attractions, changes in the area, exciting new events, or improvements to your facilities all help a guest to plan another trip to your location.


If the above list sounds lofty and you want to prioritize, you should start by focusing your efforts on emails #1, #2, and #5 to ensure that they match your messaging and branding. Also make sure that the emails scale properly for mobile devices because more and more people are tuning into their email from their mobile devices. We have found that many vacation and short term rental organizations do not capitalize on their guest email addresses & do not utilize them to cultivate a relationship of repeat business with their guests – and those organizations are missing out.

Once you’ve provided an exceptional experience, you should do everything in your power to encourage those guests to come back again. Using your WiFi to collect email addresses and automating your messaging from an email content platform may take time to set-up, but will have lasting rewards for your business. Spend the time on implementing these products and services in your organization and grow your repeat client base – you won’t be sorry that you did.

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