Should You Offer Guests an Extra Night? Here’s When (and How) to Ask

Gap nights—also known as adjacent or in-between nights—can be a goldmine for hosts, but only if you know when and how to offer them. Joanna called into the Hosting Hotline with a question we hear more and more: what’s the best timing to offer an extra night to guests—either before they arrive or after they depart?

Also called “gap nights” or “adjacent nights,” these are open calendar days that sit before or after a confirmed booking. Joanna’s running a drive-to property in Central Virginia, and like many hosts, she’s looking for ways to increase midweek bookings and boost revenue without overhauling her business model.

Here’s what we covered in the episode—and why we think every host should be offering these extra stays.

Start with Your Mindset

It’s easy to feel awkward about upselling, but offering an extra night isn’t about being salesy—it’s about hospitality. Guests are already choosing to stay with you. If there’s a chance to ease their arrival or extend their relaxation, why wouldn’t you offer it?

Whether it’s arriving a night early to set up for a family event or staying late to enjoy Sunday morning coffee without a rush, you’re giving guests more of what they already want: a seamless, stress-free experience.

When to Make the Offer

There’s no one-size-fits-all answer—but here are the three windows we recommend testing:

1. Right after booking: Especially if the guest shares why they’re visiting (wedding, reunion, birthday), you can tailor your message and offer a head start on their plans.
2. After the booking window closes: If no one else has booked the night before or after, you can trigger an offer a few days before arrival. This works well in markets with shorter lead times.
3. During the stay: Don’t underestimate a guest’s desire to linger. If they’re loving the experience, they may jump at the chance to extend—even just for a slower checkout or an extra evening by the fire.

You can experiment with all three—but start manually so you can learn what language converts. Use a spreadsheet to track what you offered, when you sent it, how the guest responded, and what the outcome was.

It’s Not Just About Timing—It’s About Framing

One of our Hosting Business Mastery coaches, Wendy, has had incredible success offering what she calls a “half-day stay.” That’s right: she doesn’t use phrases like “early check-in” or “late checkout” because they trigger objections or expectations of a freebie.

Instead, she speaks to the benefit. Want to arrive early and relax before the rest of your group shows up? Need more time to enjoy the pool before catching a late flight? A “half-day stay” can sound like a luxurious upgrade rather than a logistical add-on.

This kind of copywriting tweak matters—and can significantly impact conversion rates.

Automate Later, But Start with Data

Eventually, tools like Hostfully and Breezeway let you automate these offers with conditional logic (i.e., only send if the adjacent night is available). But automation works best once you’ve learned what your guests respond to.

So before you set up a workflow, do it the scrappy way. Write the message yourself. Adjust your language. Track what works. You’ll build a smarter system by understanding the why behind each yes or no.

Final Thoughts

Your core product isn’t a check-in guide or a welcome basket—it’s the overnight stay. Offering an extra night is the most obvious upsell in the business, and yet most hosts miss it. If you’ve got empty calendar dates before or after a stay, it’s time to stop leaving money on the table.

Whether it’s a $50 early arrival or a full extra night, those little additions add up fast. And when they’re framed with care, guests will thank you for the option.

Have More Questions? We’d love to hear from you! Submit your hosting questions to the Hosting Hotline and tune in to the podcast for answers. Don’t forget to follow us on Instagram for more tips: @thanksforvisiting_.

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Mentioned in this episode:

Hostfully | Powerful PMS with customizable guest messaging
Breezeway | Smart messaging and operations software for hosts
Thanks for Visiting Hosting Handbook | Your go-to STR resource