6 Best Upsell Software for Short-Term Rentals in 2026

For short-term rental operators, the best upsell software in 2026 is the one that carries an offer all the way to a paid, staffed outcome. Six platforms do parts of this: Conduit, Breezeway, Guesty, Enso Connect, Operto, and Touchstay. Conduit publishes a per-unit price, and the other five quote privately or take a share of each sale.

How did we rank these tools?

Ranking these tools starts from five jobs an upsell has to finish: making the offer, timing it automatically, taking payment, creating the operational work that fulfils it, and writing the result back to the property-management system. Each point comes from the vendor's own published product pages, checked in September 2026. Where a vendor does not publish something, the table says so rather than guessing. Price transparency breaks ties, because an operator comparing revenue share against a per-unit fee cannot model either one without numbers.

Which upsell software should a short-term rental manager choose?

Conduit scores five of five on the rubric above, and it publishes a per-unit price where the other five in this group do not. Guest upsells run inside the conversation the guest is already having, take payment in one click, and write the outcome back to the PMS. Packages are published at $18, $30, $36 and $48 per unit per month, with upsells included from the Guest package upward, plus a flat $899 per month Startup plan for portfolios of 0 to 25 units.

The honest watch-out is that Conduit is a communications platform first. If your upsell problem is really a housekeeping-capacity problem, Breezeway solves the operational half better.

1. Conduit

Conduit puts the offer in the message thread rather than behind an app download, captures payment with one click, and fires a workflow so the early check-in or the mid-stay clean becomes real work assigned to a real person. Published pricing: Messaging $18, Guest $30, Guest plus Devices $36, Full Suite $48, per unit per month, and a $899 per month Startup plan for 0 to 25 units. Upsells with one-click payment sit in the Guest package and above.

Best for operators who want the offer, the payment, and the follow-up task in one system. Watch out if you need deep housekeeping scheduling, which is not what this product is built around. Our guide to AI messaging tools for short-term rentals covers the wider messaging comparison.

2. Breezeway

Breezeway sends upsell offers through automated messages with purchase links, covering early check-ins, extra linens, and experiences such as bike tours and private chefs. Its Concierge agent answers routine guest questions from property details already in Breezeway and opens a task, with context pre-filled, when a guest reports something. That link between the offer and the work is the strongest in this group, because operations is what the rest of the product does.

Breezeway does not publish pricing. Managers whose upsells fail at fulfilment rather than at the offer should start here.

3. Guesty

Guesty Guest Upsells covers early check-in and late checkout, mid-stay cleaning, extra beds and cribs, breakfast baskets and restocks, and higher-end experiences like club cards and golf carts. Offers are delivered through the Guest App during the stay, with property-level pricing and a central dashboard. It runs on revenue share, and Guesty publishes the commercial terms plainly: "no setup fees, no subscription add-on, and no upfront commitment," and "you only pay when an upsell is successfully purchased."

No dollar figure is published, so the effective rate is not comparable to a per-unit fee without a quote. Best if you already run Guesty as your PMS.

4. Enso Connect

Enso Connect ships the widest named upsell catalogue here: Automated Upsells, Enso Experiences, Automated Fees, Enso Transport, an Inquiry Converter, and affiliate links to local services. The transport and experiences products go past the usual early-checkout list into things guests spend money on during a stay.

Pricing is a custom quote, described on the pricing page as "get pricing designed specifically for your portfolio." Enso publishes a return claim of "an average 4.7x return on their software spend," which is the vendor's own figure and carries no audited method. Best for operators selling experiences and transport rather than room-adjacent extras. We compare the wider product in our Enso Connect alternatives guide.

5. Operto

Operto pairs Upsells and Guest Messaging inside Operto Guest, and its distinguishing asset is the device layer: locks, thermostats, and access codes. An early check-in sold through Operto can move the door code as well as the reservation, which closes a gap that message-only tools leave to staff.

Operto does not publish pricing. The fit is portfolios already running Operto hardware, where the upsell and the access change should happen together.

6. Touchstay

Touchstay sells upsells through a widget inside the digital guidebook a guest is already reading. It is the lightest option here and the least dependent on your PMS, so a manager can run it alongside almost anything without changing systems.

Pricing sits behind a calculator rather than a published rate card. Best for small portfolios that want an upsell surface without changing their operational stack.

What features actually matter in upsell software?

The features that matter are the ones that move money and work, not the ones that fill a comparison grid. Five capabilities decide whether an upsell earns revenue or adds another message to the thread. The table below scores each platform on all five, from published sources checked in September 2026. Fulfilment is the weakest column across this group, and it is the one that turns a sale into a delivered service.

An upsell that sells a mid-stay clean without creating the clean produces a refund and an unhappy guest.

How much does short-term rental upsell software cost?

Upsell software costs are hard to compare because most vendors here do not publish a rate. Conduit publishes $18, $30, $36 and $48 per unit per month by package, plus a $899 per month Startup plan for 0 to 25 units. Guesty publishes a model but not a number, taking a share of each successful sale with no setup fee and no subscription add-on. Breezeway, Enso Connect, Operto, and Touchstay all quote privately. For a 60-unit portfolio, that means one platform you can budget from a web page and four you cannot budget until you have taken a sales call.

Revenue share and per-unit pricing carry different risks. Revenue share costs nothing when upsells do not sell and gets expensive when they do. Per-unit pricing is predictable and is paid whether or not a guest buys anything.

Does upsell software work without a PMS integration?

Upsell software runs without a PMS integration, and the missing integration costs you the part that matters most at scale. Touchstay and, to a lesser degree, Enso Connect sit beside almost any stack, which suits a manager who does not want to migrate. The trade is that a sold early check-in has to be typed into the PMS by a person, so the reservation and the money drift apart until somebody reconciles them.

Platforms that write back, including Conduit and Guesty within its own system, keep the reservation record correct without that step. For portfolios past roughly 50 units, manual reconciliation is usually where an upsell programme breaks down. Our guide to AI phone answering for vacation rentals covers the same trade on the voice side.

FAQ

The questions below come up in most evaluations we run with short-term rental operators, and the answers reflect what these products publish today rather than what is on a roadmap. Pricing transparency, fulfilment, and PMS write-back are the three that decide the shortlist for most portfolios.

What is the best upsell software for short-term rentals?

On the five-job rubric in this article, Conduit scores highest, and it is priced from a published per-unit rate card rather than a quote. Breezeway is the stronger choice when fulfilment is the bottleneck, and Guesty is the pragmatic answer for operators already running it as their PMS.

How much does short-term rental upsell software cost?

Conduit publishes $18, $30, $36 and $48 per unit per month by package, with a $899 per month Startup plan for 0 to 25 units. Guesty charges a share of each successful upsell with no setup fee or subscription add-on. Breezeway, Enso Connect, Operto, and Touchstay do not publish pricing.

Which upsell tools take payment from the guest directly?

Conduit takes payment in one click inside the conversation. Guesty collects through the Guest App on a revenue-share basis. Breezeway sends purchase links in automated messages. Enso Connect and Touchstay both take payment through their guest-facing surfaces.

Do upsell platforms create the work after a guest buys?

Conduit fires a workflow that turns the purchase into an assigned task, and Breezeway creates a task with context already filled in. Guesty, Enso Connect, and Touchstay do not publish a fulfilment step, so the operational half stays with your team unless another tool picks it up.

Which upsells sell best in short-term rentals?

Guesty publishes the clearest list: early check-in and late checkout, mid-stay cleaning, extra beds and cribs, breakfast baskets and restocks, and higher-end experiences. Enso Connect adds transport and local experiences. Nobody in this group publishes audited conversion rates, so treat vendor revenue claims as unaudited.

Can I run upsells without switching my PMS?

Yes. Touchstay and Enso Connect are designed to sit alongside an existing stack, and Conduit connects to property-management systems rather than replacing one. Guesty upsells require Guesty as the PMS, since the feature is embedded in that platform.

What should a 60-unit operator budget?

Only two of these platforms let you answer that before a sales call. Conduit publishes per-unit packages, so 60 units on the Guest package is a figure you can calculate directly. Guesty's revenue share scales with sales rather than doors, which is cheaper at low volume and less predictable at high volume.