Problems
How Do I Fill the Shoulder Season?
Shoulder season bookings come from three sources: guests who are flexible on timing and respond to reduced rates, past guests you invite back with specific offers, and travellers who have a reason to visit off-peak (events, conferences, local activities). The key is light discounting (10 to 20 percent) paired with direct outreach and creating genuine reasons to book, not deep discounting that trains guests to avoid peak rates.
Understand what actually happens in shoulder season
Shoulder season is when your market naturally slows down: May and September for ski towns, April and October for beach destinations, or winter for most regions. These periods are slower because demand genuinely drops, not because your property is broken. Understanding that helps you avoid panic pricing.
The guests who do book in shoulder season are usually more price-sensitive and flexible, but they are also often better guests: retirees on fixed schedules, remote workers escaping the city, or people visiting for specific local events (conferences, festivals, birthdays). They are less likely to party, more likely to leave the property clean, and more likely to become repeat guests or refer others. Shoulder season guests also often book longer stays, which can mean better margins despite the lower nightly rate.
Price strategically and use direct outreach to past guests
A light discount (10 to 20 percent off peak rate) during shoulder season attracts flexible guests without signalling that your property is a last resort. Deep discounts (40 to 50 percent) can work short term, but they train guests to wait for the discount and erode the perception of your true value. If your peak rate is $150 a night, offering $130 a night for April bookings is far smarter than dropping to $85.
Limit the discount to a date range (e.g., April 1 to 15 only) rather than leaving it open-ended. This creates urgency and also signals that the discount is temporary and tied to the low season, not a permanent repricing. Your best source of shoulder season bookings is guests you have already hosted. They know your property, trust you, and many would return if given a reason. If you collect email addresses (you should), send a personal message in April offering a spring discount or a specific reason to return (e.g., "Easter holidays", "ANZAC weekend", "school holidays"). Frame it as an invitation, not a sales pitch. Offer bigger discounts to guests from two or more years ago (more likely to need a nudge), and smaller discounts to guests from the previous year (they already know the value).
Build local partnerships and create reasons to visit
Shoulder season demand increases if there is something to do off-peak. Partner with local businesses: offer a discount bundle (stay at your bach, eat at a local restaurant, book a tour) that gives guests a reason to visit. Sponsor or feature local events on your website and in booking confirmations. A property in a ski town can promote autumn hiking and mountain biking; a beach house can promote dolphin spotting or birdwatching in winter.
These partnerships do not need to be formal or costly. A single paragraph in your listing describing what to do in shoulder season, linked to specific attractions, restaurants or local guides, makes a material difference. Guests often avoid off-peak travel because they assume there is nothing to do, not because accommodation is actually unavailable. Concrete suggestions move the needle: instead of "lots to do in autumn", say "April is perfect for hiking the Roys Peak track or visiting the local vineyard just 15 minutes away". Also track which partnerships work: if a guest books after learning about a specific local activity, note that. You now know what to promote next shoulder season. Some partnerships can even generate extra revenue: if a local tour operator brings guests your way, negotiate a small commission on bookings they generate.
Use platform visibility tools and direct channels effectively
On major platforms, seasonal promotions often come with a visibility boost. A 14-day 20 percent discount promotion might get your listing featured higher in searches during that period, which brings more eyes to the property beyond just the discount-seekers. Test it and measure the result: did bookings increase beyond what the discount alone would predict? Also check whether you have accidentally changed your minimum stay, blackout dates, or availability in a way that is hiding you from searches during shoulder season.
If you have a direct booking website, shoulder season is when the advantage becomes clear. Platform algorithms may bury your listing to favour seasonal bestsellers, but your own website is always searchable. Email past guests, run a simple social media reminder, or list on Google Business Profile. Direct channels often yield more shoulder season bookings with better margins than chasing platform visibility with deep discounts. You also build a relationship and email list that you control, which means your shoulder season strategy does not depend on an algorithm you cannot influence.
Document and refine your shoulder season playbook
Shoulder season strategies are worth documenting and testing year over year. Keep records of which discounts worked (which month, which discount percentage, how many bookings resulted), which partnerships were productive, and which guest outreach messages got responses. This becomes your playbook: in April of next year, you run the same campaign that converted last April.
Shoulder season is also an opportunity to test new pricing models or property improvements with lower stakes. If you are thinking about adding a hot tub or upgrading wifi, shoulder season with lighter bookings is the time to do it. You can position the upgrade in your marketing for next year's shoulder season with new photos and amenities listings. Over time, a segment of your past guests will become reliable shoulder season repeat bookers, and you will have built a sustainable rhythm of bookings across the entire year instead of feast and famine patterns.
Want to see what a finished direct-booking site actually looks like? Tideline House is a full live example, built the same way we would build yours.
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