5stelle vs Chekin: Head-to-Head Comparison
TL;DR: 5stelle and Chekin both target short-term rental operators. Pick **[5stelle](/5stelle-review/)** if: Italian accommodation operators — hotels, B&Bs, and short-term rentals — who need an all-in-one PMS with native integrations for Italian police registration, ISTAT reporting, and electronic invoicing. 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…
Category: Property Management Software · 5stelle · Chekin
At a glance
| 5stelle | Chekin | |
|---|---|---|
| Category | Italian cloud PMS covering hotels, B&Bs, and short-term rentals | Guest registration and automated tax reporting for STRs in regulated European markets |
| Founded | 2011 | 2017 |
| HQ | Italy | Valencia, Spain |
| Pricing | subscription | from $4/mo |
| Best for | Italian accommodation operators — hotels, B&Bs, and short-term rentals — who need an all-in-one PMS with native integrations for Italian police registration, ISTAT reporting, and electronic invoicing. | 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. |
| Overall | 5.5/10 | 6.8/10 |
Feature-by-feature
| Feature | 5stelle | Chekin |
|---|---|---|
| Channel manager | ✅ Native | — |
| Unified inbox | ⚠️ Partial | — |
| Direct booking site | ✅ Native | ⚠️ Partial |
| Task management | ⚠️ Partial | — |
| AI guest messaging | — | — |
| AI that takes actions | — | ⚠️ Partial |
| Automation rules | ⚠️ Partial | ✅ Native |
| Pricing optimizer | 🔌 Via integration | — |
| Open API | ⚠️ Partial | ✅ Native |
| Mobile app | ✅ Native | ✅ Native |
| Multi-calendar | ✅ Native | — |
| Accounting / reporting | ✅ Native | ⚠️ Partial |
| Revenue management | ⚠️ Partial | — |
Scores by dimension
| Dimension | 5stelle | Chekin |
|---|---|---|
| Ease of use | 6/10 | 7/10 🏆 |
| Features depth | 7/10 | 7/10 |
| Value for money | 7/10 | 8/10 🏆 |
| Support | 7/10 | 7/10 |
| AI capability | 2/10 | 5/10 🏆 |
| Scalability | 6/10 | 7/10 🏆 |
| Learning curve | 5/10 | 6/10 🏆 |
| Pricing transparency | 4/10 | 7/10 🏆 |
Where 5stelle wins
- Channel manager — native in 5stelle, not in Chekin
- Multi-calendar — native in 5stelle, not in Chekin
Where Chekin wins
- AI capability — 5/10 vs 2/10
- Pricing transparency — 7/10 vs 4/10
Which one should you pick?
Pick 5stelle if: Italian accommodation operators — hotels, B&Bs, and short-term rentals — who need an all-in-one PMS with native integrations for Italian police registration, ISTAT reporting, and electronic invoicing. 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 by operator profile
| Profile | Winner | Why |
|---|---|---|
| Solo host (1-5 units) | Chekin | Higher profile fit (6.8 vs 5.5). |
| Boutique operator (6-20 units) | Chekin | Higher profile fit (7.2 vs 5.6). |
| Professional PM (20+ units) | Chekin | Higher profile fit (7.3 vs 5.9). |
| Enterprise (100+ units) | Chekin | Higher profile fit (7.2 vs 5.7). |
| Multi-market operator | Chekin | Higher profile fit (7.2 vs 5.4). |
| Tech-forward, AI-first | Chekin | Higher profile fit (7.0 vs 4.3). |
| Budget-conscious | Chekin | Higher profile fit (7.4 vs 5.9). |
5stelle in one paragraph
5stelle — Italian cloud PMS covering hotels, B&Bs, and short-term rentals. Strengths: Italian-market depth — Alloggiati Web, ISTAT, e-invoicing built in; Covers hotels, B&Bs, and STRs from one platform; Cloud-based with native mobile app. Weaknesses: Primarily IT-focused — less polish outside the Italian market; AI features are minimal versus global competitors. Full 5stelle review →
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 →
See also
- All Property Management Software comparisons
- 5stelle vs AirDNA
- AirDNA vs Chekin
- 5stelle vs Amenitiz
- Amenitiz vs Chekin
- 5stelle vs AvaiBook
- AvaiBook vs Chekin
FAQ
Is 5stelle or Chekin cheaper?
Chekin publishes entry-level pricing; 5stelle requires a sales call, so the answer depends on the quote you get.
Does 5stelle have better AI than Chekin?
Chekin scores higher on ai capability — 5/10 vs 2/10.
Which is easier to use, 5stelle or Chekin?
Chekin scores higher on ease of use — 7/10 vs 6/10.
Can I switch from 5stelle to Chekin?
Yes, but plan for migration cost: channel reconnections, template rebuilds, automation recreation, and team retraining. Both 5stelle and Chekin export reservation history; neither exports their automation rules cleanly. Run both in parallel for at least two weeks before cutting over.