Strategic Upselling for the Holiday Season: How Hoteliers Can Prepare

As the holiday season gets underway, many hotels face the challenge of maximizing revenue while improving the guest experience. With upselling, this presents a real opportunity, but it requires a comprehensive strategy beyond just offering room upgrades. A structured approach is necessary for hotel revenue to grow—including planning, preparation, and data-driven execution.

Let’s explore some essential steps to develop a holiday upselling strategy that elevates the guest experience and drives tangible value to your bottom line.

Step 1: Analyze Data from Past Holiday Seasons

Start by reviewing data from previous holiday seasons. This will give you insights into which upsells were most popular, which guest segments were most receptive, and when guests were most likely to upgrade. Identifying trends and patterns will inform your approach this year.

• What were the top-selling upsells last year? Did guests gravitate toward room upgrades, F&B offerings, or holiday experiences? This insight helps refine what worked and what didn’t.
• Which guest segments converted the most? Did families, business travelers, or couples engage more with upsell offers?
• When did guests book upgrades? Timing is key. For Pre-Arrival: did more holiday guests upgrade when offers were sent further or closer to their arrival date?  For On Arrival: holiday season is great for upselling, so if your results did not grow analyze why.  For In-stay: did you adjust your offers based on the holiday experiences and what timing were offers best engaged with - morning, afternoon, or evening? Adjust your approach based on these patterns.

Step 2: Develop Special Holiday-Themed Offers

With data in hand, it’s time to create specific, holiday-themed offers that go beyond typical upselling and make the guest’s stay extra special.

• Holiday Room Enhancements: Go beyond a standard room upgrade by offering themed holiday suites where guests can select decorations for their room—Christmas trees, festive lights, games, or even holiday scents. 
• Seasonal F&B Packages: Develop exclusive food and beverage offerings, such as Christmas Eve dinners, New Year’s champagne breakfasts, or holiday-themed afternoon teas. Collaborate with your culinary team to create menus that evoke the spirit of the holidays. Offer them as a bundle with room packages or as standalone options.
• Local Experience Add-ons: The holiday season often coincides with local events, festivals, and markets. Partner with local businesses to offer guests exclusive access or discounts, adding a local touch to their stay. 

Step 3: Build a Guest-Centric Upselling Timeline

Upselling should never feel intrusive, especially during the holidays. Thoughtfully timing your offers ensures they feel natural and well-received.

• Pre-Arrival: The best time to upsell is often before the guest arrives. Send personalized emails in the weeks leading up to their stay, showcasing holiday offers such as room upgrades, dining experiences, and seasonal activities. Upselling automation tools help tailor these emails based on guest preferences and booking history.
• On-Arrival: Train front desk staff to offer upgrades in a way that feels more like an enhancement than a sales pitch. A warm holiday greeting followed by a limited-time offer—like upgrading to a festive suite—can make the guest feel valued while boosting conversion rates.
• In-Stay: Don’t stop upselling once the guest checks in. Use in-room tablets, mobile apps, or guest services platforms to suggest upgrades throughout their stay. A well-timed offer for a festive room service menu, spa treatment, or late checkout can appeal to guests immersed in the holiday spirit.

Step 4: Empower and Train Your Staff

An upselling strategy is only as strong as the team executing it. Your upselling strategy will only work if your staff is aligned and confident.

• Product Knowledge: Ensure your staff knows all the holiday-specific upsell options, including package details, pricing, and availability. They should understand how each offer enhances the guest experience.
• Scenario-Based Training: Move beyond scripts by using real-world scenarios where staff can practice upselling during organic interactions. For example, a front desk agent could say, “We’ve prepared a special festive upgrade with a beautifully decorated room and an in-room holiday breakfast. How would you like to make your stay even more festive?”
• Incentivize Your Staff: Motivate your team with seasonal upselling incentives, such as bonuses or prizes for those who achieve the most sales. Make it more exciting by doing instant rewards for daily or weekly target achievements. A motivated staff will bring energy and enthusiasm to guest interactions, improving both upselling success and guest satisfaction.

Step 5: Leverage Technology for Smarter Upselling

Data-driven technology and automation can ensure that your upselling efforts are timely, relevant, and efficient, without overwhelming your staff.

• Automated Pre-Stay Offers: Send personalized, automated upsell offers before guests arrive. Personalized offers typically see higher conversion rates.
• In-Stay Upselling via digital channels: Hotels using mobile apps, QR codes, or SMS can send real-time push notifications offering upgrades like holiday meals, in-room dining, or last-minute experiences. The convenience of online booking makes these offers more likely to convert.

Step 6: Measure, Adjust, and Optimize

Once your holiday upselling strategy is in place, track and measure results so you can adjust your approach in real time and gather valuable insights for future seasons.

• Monitor Upsell Conversions: Track the performance of each campaign and note which offers convert best. Use this data to adjust as needed—for instance, if room upgrades are underperforming, bundle them with other popular holiday experiences.
• Collect Guest Feedback: Solicit feedback from guests who accepted or declined upsell offers. Get insights into how your offers are being received and where there’s room for improvement.
• Optimize for Future Seasons: The insights gained this holiday season will help you refine your strategy for next year. 

Final Thoughts

The key to successful upselling during the holidays isn’t about pushing products—it’s about delivering a personalized guest experience they will remember. By strategically planning, training your staff, and leveraging the right technology, you can create an upselling strategy that enhances guest satisfaction and revenue.

Let UpsellGuru help you prepare now to set your hotel up for a successful, guest-centric holiday season. Connect with us for a free demo!