Repeat Guests Are Your Most Profitable Bookings — Here's How Maine STR Hosts Keep Them

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The Guests Who Come Back Are Your Best Guests — Here's How to Keep Them

There's a guest type every Maine short-term rental host quietly hopes for: the one who comes back.

They know where to park. They know your quirks. They take care of the place because they care about it. They leave glowing reviews without being asked. And when May rolls around, they're already thinking about booking their summer trip.

Repeat guests don't happen by accident. They happen when hosts make them feel like more than a transaction. Here's how to do that — and why it makes financial sense too.

Send a personal thank-you after checkout

Most hosts send automated messages. Almost none send a genuine, personal note after a guest leaves.

‍It doesn't have to be long. A few sentences using the guest's name, referencing something specific about their stay ("Hope the lobster shack was as good as we promised!"), and wishing them well goes further than any automated follow-up.

‍This is the moment to plant the seed of a return visit. Something as simple as "We'd love to have you back next summer" is enough — and it costs nothing.

‍ ‍Keep a simple record of returning guests

You don't need a CRM for this. A basic notes document or spreadsheet is enough.

When a guest books again, a quick note from their last stay — their preferred check-in time, what brought them to Maine, a milestone they mentioned — lets you personalize their experience in a way that genuinely surprises people.

‍Here's the bookkeeping parallel: the same habit of keeping clean, organized records that makes a guest feel remembered is exactly what protects you financially. Hosts who track their guests carefully tend to track their income and expenses carefully too — and that pays off at tax time.

‍ ‍Offer a small returning-guest perk — and track it

‍The perk doesn't have to be monetary. Early check-in when you can swing it, a handwritten welcome-back card, a local product left on the counter — these small gestures cost very little and create outsized goodwill.

‍ If you do offer a discount or leave a welcome gift, record it. Guest appreciation expenses — welcome baskets, local products, small gifts — are legitimate business expenses and potentially tax deductible. Most hosts leave this money on the table simply because they don't track it.

Make it easy to rebook — and understand what direct bookings mean for your bottom line

‍Friction kills repeat bookings. If a guest has to search for your listing all over again, navigate a platform, and re-enter all their information, many of them just won't.

Wherever possible, make the path back simple — a direct booking link, your listing name clearly communicated, or a proactive outreach when your calendar opens for the following year.

‍ There's also a real financial reason to encourage direct bookings: Airbnb and VRBO typically charge host fees of 3–5% per booking. On a $2,000 booking, that's up to $100 back in your pocket when a repeat guest books directly. Over a full season of returning guests, those savings add up meaningfully — and they should show up clearly in your books.

Why repeat guests matter more than you might think — financially

Repeat guests aren't just easier — they're more profitable. They typically leave better reviews, communicate more clearly, and take better care of your property than first-time guests.

‍But here's something most hosts don't measure: the actual cost of acquiring a new guest versus retaining an existing one. New guests often come through paid platforms with higher fees. First-time guests sometimes require more communication, more cleaning time, and carry more uncertainty. When you look at your numbers closely, a loyal returning guest is often your highest-margin booking of the season.

‍In a market like Maine, where seasonality is real and summer competition increases every year, a core group of returning guests is one of the most valuable — and most underappreciated — assets your rental business has.

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Want to know which of your bookings are actually most profitable? Clean, organized books make that question easy to answer. McAfee's Bookkeeping offers a free review of your rental finances — no obligation, just clarity. Schedule a free consultation here.

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