Chekin vs Hostaway: Head-to-Head Comparison
TL;DR: Chekin and Hostaway both target short-term rental operators. Pick **[Chekin](/chekin-review/)** if: Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. Pick **[Hostaway](/hostaway-review/)** if: Operators who want a proven mid-market PMS with broad channel integrations, owner portals, and automation out of the box.
Category: Property Management Software · Chekin · Hostaway
At a glance
| Chekin | Hostaway | |
|---|---|---|
| Category | Guest registration and automated tax reporting for STRs in regulated European markets | Mid-market PMS with the highest-status OTA connections and unified inbox |
| Founded | 2017 | 2015 |
| HQ | Valencia, Spain | Toronto, Canada |
| Pricing | from $4/mo | quote-based |
| Best for | Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. | Operators who want a proven mid-market PMS with broad channel integrations, owner portals, and automation out of the box. |
| Overall | 6.8/10 | 6.2/10 |
Feature-by-feature
| Feature | Chekin | Hostaway |
|---|---|---|
| Channel manager | — | ✅ Native |
| Unified inbox | — | ✅ Native |
| Direct booking site | ⚠️ Partial | ✅ Native |
| Task management | — | ✅ Native |
| AI guest messaging | — | ⚠️ Partial |
| AI that takes actions | ⚠️ Partial | — |
| Automation rules | ✅ Native | ✅ Native |
| Pricing optimizer | — | 🔌 Via integration |
| Open API | ✅ Native | ✅ Native |
| Mobile app | ✅ Native | ✅ Native |
| Multi-calendar | — | ✅ Native |
| Accounting / reporting | ⚠️ Partial | ⚠️ Partial |
| Revenue management | — | ⚠️ Partial |
Scores by dimension
| Dimension | Chekin | Hostaway |
|---|---|---|
| Ease of use | 7/10 | 7/10 |
| Features depth | 7/10 | 8/10 🏆 |
| Value for money | 8/10 🏆 | 7/10 |
| Support | 7/10 | 7/10 |
| AI capability | 5/10 | 5/10 |
| Scalability | 7/10 | 8/10 🏆 |
| Learning curve | 6/10 | 6/10 |
| Pricing transparency | 7/10 🏆 | 2/10 |
Where Chekin wins
- Pricing transparency — 7/10 vs 2/10
Where Hostaway wins
- Channel manager — native in Hostaway, not in Chekin
- Unified inbox — native in Hostaway, not in Chekin
- Task management — native in Hostaway, not in Chekin
- Multi-calendar — native in Hostaway, not in Chekin
Which one should you pick?
Pick Chekin if: Operators in Spain (Registro de Viajeros / Parte de Viajeros), Italy (Alloggiati Web), Portugal (SEF/SEF.HOS), and France (taxe de séjour) who need automated police registration and tourist-tax reporting that would otherwise be manual, error-prone, and legally risky. Pick Hostaway if: Operators who want a proven mid-market PMS with broad channel integrations, owner portals, and automation out of the box.
Pick by operator profile
| Profile | Winner | Why |
|---|---|---|
| Solo host (1-5 units) | Chekin | Higher profile fit (6.8 vs 6.2). |
| Boutique operator (6-20 units) | Chekin | Higher profile fit (7.2 vs 7.0). |
| Professional PM (20+ units) | Hostaway | Higher profile fit (7.6 vs 7.3). |
| Enterprise (100+ units) | Hostaway | Higher profile fit (7.7 vs 7.2). |
| Multi-market operator | Hostaway | Higher profile fit (7.6 vs 7.2). |
| Tech-forward, AI-first | Hostaway | Higher profile fit (7.2 vs 7.0). |
| Budget-conscious | Chekin | Higher profile fit (7.4 vs 5.7). |
Chekin in one paragraph
Chekin — Guest registration and automated tax reporting for STRs in regulated European markets. Strengths: Only guest-experience tool with deep, country-specific legal-registration coverage across Spain, Portugal, Italy, France, Germany, and more — a genuine regulatory moat; Automated filing to government portals (Registro de Viajeros, Alloggiati Web, SEF) replaces daily manual paperwork; Automated tourist-tax calculation, collection, and remittance by jurisdiction. Weaknesses: Narrow geographic sweet spot — value collapses outside regulated EU markets; Guest-experience layer (messaging, upsells) is thinner than Duve or Enso Connect — most operators pair Chekin with one of those. Full Chekin review →
Hostaway in one paragraph
Hostaway — Mid-market PMS with the highest-status OTA connections and unified inbox. Strengths: Highest-status OTA connectivity (Airbnb, Vrbo, Booking.com, Google); Unified inbox with SLA tracking, templates, team assignments, AI replies; Solid direct-booking website builder with conversion widgets. Weaknesses: Pricing is not public; AI scope beyond messaging is lightly documented. Full Hostaway review →
See also
- All Property Management Software comparisons
- 5stelle vs Chekin
- 5stelle vs Hostaway
- AirDNA vs Chekin
- AirDNA vs Hostaway
- Amenitiz vs Chekin
- Amenitiz vs Hostaway
FAQ
Is Chekin or Hostaway cheaper?
Chekin publishes entry-level pricing; Hostaway requires a sales call, so the answer depends on the quote you get.
Does Chekin have better AI than Hostaway?
Chekin and Hostaway score equally on ai capability (5/10).
Which is easier to use, Chekin or Hostaway?
Chekin and Hostaway score equally on ease of use (7/10).
Can I switch from Chekin to Hostaway?
Yes, but plan for migration cost: channel reconnections, template rebuilds, automation recreation, and team retraining. Both Chekin and Hostaway export reservation history; neither exports their automation rules cleanly. Run both in parallel for at least two weeks before cutting over.