Upsells can be a great revenue booster, but there’s a difference between guests feeling sold to versus cared for.— a distinction that often comes down to timing and psychology. Think of a luxury hotel: the front desk doesn’t apologize for mentioning spa services or room upgrades. Instead, they frame these options as ways to enhance your experience.
Short-term rental hosts can learn from this approach. Full-service hotels generate approximately thirty percent of their revenue from services offered after the initial booking. While STR guests have different expectations, the underlying psychology remains the same: guests are willing to pay for convenience and memorable experiences during their travels.
The key lies in understanding when and how to introduce these services without damaging the guest relationship or making them feel over-pressured. Done right, the positive impact is significant. Well-timed and strategically placed upsells can make guests feel truly welcome, that spending extra on your offerings is worthwhile, and that they’ve truly enhanced their experience.
We recently discussed how to get upsells just right with Annie Sloan from The Host Co. and Julie Mallett from The Haven WNC.
You can watch the entire conversation here.
Reframing upsells as hospitality
Many property managers have what The Host Co.’s Annie Sloan calls a “knee-jerk reaction” to upsells, not wanting to sell anything to their guests. This mindset stems from a fear of appearing pushy or transactional.
But there’s a crucial distinction between nickel-and-diming guests (charging for coffee or a toothbrush) and offering genuine enhancements. Certain services can be positioned as going above and beyond for guests rather than as profit opportunities.
Consider the difference between charging a pet fee and offering a “deluxe pet experience,” says Annie. “People’s pets are their babies. If you offer them a deluxe experience instead of a pet fee, with two bowls that say Sedona, Arizona, and a little handkerchief, they will absolutely love that.”
The anticipation effect
One of the most surprising insights into the psychology of travel is that many travelers experience more joy from anticipating and planning their trip than from the trip itself.
This anticipation has powerful implications for how you introduce additional services. Even if guests don’t actually book certain offerings, simply knowing they’re available can enhance their overall experience and perception of your property.
“Your guest is likely never going to book a yacht charter, but because they know it’s available, they already feel stronger,” says Annie. “They’re already likely gonna give you a better review.”
This anticipation effect means that introducing services early in the booking process serves multiple purposes beyond generating immediate revenue. It helps build a picture of your property and what guests can expect from you and your services.
The three critical timing windows
Window 1: post-booking socialization
The first opportunity to introduce additional services comes immediately after booking confirmation. This isn’t about making immediate sales; it’s about making your guests aware of what’s available.
The goal is similar to airline upsells for rental cars. Most people won’t book immediately, but you’re establishing awareness and providing a reference point for future inquiries.
Window 2: pre-arrival excitement
The second crucial timing window takes place one week before arrival. Annie explains that this coincides with the peak phase of trip planning and excitement, and helps build anticipation.
This timing works because:
- Many services require booking in advance, especially in rural areas
- Guests are actively planning their itinerary
- Anticipation is at its highest point
- There’s still time to arrange memorable experiences
Window 3: convenience during stay
The final window involves check-in and during-stay communications. These should focus on convenience and spontaneous needs rather than planned experiences.
A simple nudge right after check-in to share available services can help capture last-minute requests or address unexpected situations.
Messaging that builds trust
The language that you use when introducing extra services significantly impacts guest perception. Remember, the goal is to sound helpful rather than sales-focused.
Effective approaches include:
- We have these services available if you’re interested
- Here’s what we can connect you with
- Previous guests have enjoyed these local experiences
- Let us know if you’d like to add any upgrades
Avoid language that creates pressure:
- Don’t miss out on
- Limited-time offer
- Most guests purchase
- Highly recommended
Julie Mallett, who owns The Haven in Western North Carolina, demonstrates this principle in action. She describes her offerings as add-ons and focuses on how they enhance the guest experience rather than generate revenue.
“Guests absolutely love the add-ons,” Julie says. “They rave about them. They are talking about them on social media posts, in the reviews.” One guest on a romantic honeymoon getaway had the following to say: “What truly made our stay exceptional was the host’s outstanding responsiveness. Julie was incredibly communicative, friendly, and went above and beyond to ensure we had everything we needed.”
In other words, good add-ons that are a fit for your property and location can sell themselves. Guests want to have a good time, and if you’re offering the right activities or extra amenities, and are attentive to their needs they will jump at the opportunity with excitement.
Avoiding the brochure rack problem
One common mistake is overwhelming guests with too many options. Annie warns against becoming “the brochure rack at a Best Western” with ninety different offerings.
Instead, curate services based on:
- Your target market’s interests
- Past guest requests and feedback
- Local strengths and unique offerings
- Seasonality
Julie’s properties focus on couples’ experiences in a remote mountain setting, offering romance packages and pop-up picnics rather than trying to appeal to every possible guest type.”We really researched our target market, and we have curated the experiences for that target,” she says.
What to avoid
Surprise costs
Transparency about pricing prevents post-stay disappointment and negative reviews. If late checkout costs $20 per hour, communicate this information upfront.
Guests appreciate knowing costs in advance, even if they choose not to purchase additional services.
Over-communication
Finding the right communication frequency prevents guest fatigue. The three-window approach provides structure without overwhelming guests with constant service promotions. Don’t bombard your guests with information on add-ons.
Remember, quality amenities are an easy sell. They improve the guest experience and typically offer something guests were already hoping to find.
Mismatched expectations
Services should align with your property type and guest demographics. Luxury wellness retreats and budget cabins require different approaches to additional services. If your property is a downtown city apartment marketed to business travelers, don’t offer hiking gear rentals or nature photography sessions; instead, focus on services like airport transfers, late checkout, or premium coffee delivery that actually match their urban, convenience-focused needs.
Building long-term value through strategic upselling
Well-executed service offerings create compounding benefits that extend beyond immediate revenue and can promote positive word-of-mouth, as well as opportunities to share on social media.
The social media amplification effect also drives future bookings. When guests share photos and stories about unique experiences, they create organic marketing content that showcases your property’s distinctive offerings.
Implementation strategy
A simple three-step approach works best:
- Identify 3–5 services that match your guest profile and location.
- Create messaging templates for each stage of the guest journey.
- Track which communications drive the most engagement and bookings.
Remember, success isn’t just about conversions. Services that aren’t purchased can still enhance satisfaction, boost reviews, and create referral opportunities. The key is genuine hospitality: when guests feel cared for rather than sold to, they’re more likely to book extras, leave positive feedback, and recommend your property.
Want to dive deeper into these strategies?
Watch the full recording of our online event here and explore how to put them into practice.