How Oaky helps fill premium rooms without discounting them

The Opportunity

Premium rooms aren’t just higher-priced inventory; they’re a powerful lever for both revenue and reputation.

Premium rooms can also create better experiences for your guests. Guests who stay in them enjoy more high-end amenities, extra convenience and have a better experience overall. That’s why they’re usually happier with their stay and more likely to rave about it online.

However, when premium rooms remain empty, their value takes a hit. They cost more to build, furnish and maintain, yet they’re the last to be filled. The same holds true when you give them away for free. What’s worse, your guests start to expect luxury at no cost.

In short, treating premium rooms as an afterthought won’t get you far; it’s time to start managing them as strategic assets, and upselling with Oaky can play a key role.

The Challenge

Despite their value, premium rooms often go unbooked. To fill these rooms, hotels have to discount them, or even worse, give them away for free to make up for overbooked standard rooms. In both cases, you miss out on potential revenue and the opportunity to make guests’ stay better.

But why are they often left underused?

Because most guests book standard rooms by default, leaving suites and high-end categories underutilized. Most guests default to standard rooms when booking because they’re still in budgeting mode —they go for cheaper flights, transfers, and base costs are top of mind.

What’s more, premium options are rarely presented at the right moment, and without understanding the added value, guests tend to stick with the safe, familiar choice.

However, once these essentials such as flights and accommodation are paid for, guests shift into experience mode, where they prioritize comfort, convenience and making the most of their trip --> that's the right moment to offer extras and upgrades.

The Solution

With Oaky, you can upsell more premium rooms through automated, personalized upgrades offered to guests pre-arrival and at check-in.

How it works:

1. Pre-arrival offers

Let’s say someone books a standard room. Before their arrival, Oaky automatically sends a selection of personalized offers, including premium room upgrade options, for example:

• “Upgrade to a Junior Suite with Sea View for just an extra $40/night”

• “Treat yourself to a Signature Suite with welcome champagne.”

This way, hotels can inform guests about all available options at the right moment of the guest's journey. Many guests don’t even realize they have the opportunity to upgrade — and when they do, many are happy to pay more to make their stay extra special. These offers reach guests at a key decision-making moment when travel plans are set, flights secured and paid for, and guests are more open to splurging on an upgrade that feels worth it.

Strategically, this builds revenue before arrival and reduces pressure on front desk staff to close upgrades in the moment. And, the hotel can resell standard rooms.

2. Upselling at check-in

Upselling at the front desk is your second chance. Oaky helps your team offer relevant upgrades based on who's checking in and what’s available. Agents get suggestions right from the software, so they can focus on high-value offers without the guesswork.

What’s more, Oaky includes the unique selling points for each upgrade and service, so the agent knows what to upsell and can flip the screen to showcase offers to the guest right in front of them, making it more visual.

With Oaky, you can also set up an incentive program to reward the team for successful upsells. When upselling at check-in, they can see how much they can earn from each upsell, which keeps them focused on selling more high-margin deals, such as room upgrades. It creates a win-win for your employees and guests. Your team feels more motivated, while your guest can enjoy a better room.

How to maximize your results with smart upselling automation

Oaky’s platform gives you the flexibility to test and refine your upselling strategies. Creating deals is just the beginning—there’s much more you can do to personalize offers and boost guest engagement.

1. Segment your guest communication by guest profile or booking channel

Use Oaky’s robust segmentation to match the right offer to the right guest. Business travelers and families have different needs, so a one-size-fits-all approach doesn’t work. By tailoring your upsells to specific segments before arrival, you increase conversion potential.

Tip: Use Chain Dashboard Segmentation to apply this at scale across multiple properties.

2. Use dynamic pricing instead of fixed-price upgrades

When it comes to selling rooms, dynamic pricing is not a new tactic. But have you tried it for upselling? With Oaky, you can align upgrade rates with your existing revenue strategy or create a custom approach. This flexibility helps maximize revenue during high-demand periods and optimize performance during quieter times.

3. Create packages to enhance perceived value

Hotels offering packages often see higher upsell conversion rates than those offering single add-ons. Packaging multiple add-ons into one offer increases perceived value and simplifies guest decision making. Guests are more likely to purchase when they see clear benefits and cost savings in a bundle versus evaluating individual items separately.

4. Train your team sell benefits and experiences, not features

Upselling success depends on how offers are presented. Focus on benefits, not specs. Instead of highlighting “extra square meters,” describe the comfort and relaxation of a spacious room with a private balcony. Emotion-driven messaging helps guests visualize the experience—and motivates them to upgrade.

Tip: Emphasize how the offer will enhance their stay, not just what it includes.

5. Measure upsell success beyond revenue

Revenue is just one part of the upselling equation. Since upselling enhances the entire guest journey, success should also be measured through repeat bookings, review scores, and overall guest satisfaction.

Guests who feel understood and valued are more likely to return and leave positive feedback. Over time, this drives loyalty, boosts your online reputation, and strengthens your hotel’s long-term performance.

The result

Filled premium rooms, no more free upgrades, and more delighted guests.

Many of our customers report this positive change since implementing Oaky.

For example, Clarion Hotel Karlatornet (a 4-star hotel based in Gothenburg, Sweden) has highlighted the effectiveness of Oaky to upsell their premium rooms, such as rooms on Level 58, located 200 meters above ground with breathtaking views. As mentioned by their Front Office Manager, Oliver Niskanen, these rooms are always in high demand, and guests are more than happy to pay for a stunning view and secure a premium room in advance thanks to Oaky.

Final thoughts

You don’t have to discount your premium rooms to make them appealing. The first step to filling them is making your guests aware of the opportunity to upgrade. A combined approach of presenting these opportunities at pre-arrival and at the front desk has proven to be the most effective, reaping financial benefits for hotels and making guests’ stays truly elevated.