Chekin vs RoomRaccoon: Head-to-Head Comparison
TL;DR: Chekin and RoomRaccoon 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 **[RoomRaccoon](/roomraccoon-review/)** if: Small independent hotels and B&Bs in Europe or South Africa wanting PMS + channel manager + booking engine + payment processing in one subscription.
Category: Property Management Software · Chekin · RoomRaccoon
At a glance
| Chekin | RoomRaccoon | |
|---|---|---|
| Category | Guest registration and automated tax reporting for STRs in regulated European markets | All-in-one hotel management system for small independent hotels and B&Bs |
| Founded | 2017 | 2017 |
| HQ | Valencia, Spain | Breda, Netherlands |
| Pricing | from $4/mo | from $188/mo |
| 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. | Small independent hotels and B&Bs in Europe or South Africa wanting PMS + channel manager + booking engine + payment processing in one subscription. |
| Overall | 6.8/10 | 6.2/10 |
Feature-by-feature
| Feature | Chekin | RoomRaccoon |
|---|---|---|
| Channel manager | — | ✅ Native |
| Unified inbox | — | ⚠️ Partial |
| Direct booking site | ⚠️ Partial | ✅ Native |
| Task management | — | ⚠️ Partial |
| AI guest messaging | — | ⚠️ Partial |
| AI that takes actions | ⚠️ Partial | ⚠️ Partial |
| Automation rules | ✅ Native | ✅ Native |
| Pricing optimizer | — | ⚠️ Partial |
| Open API | ✅ Native | ⚠️ Partial |
| Mobile app | ✅ Native | ⚠️ Partial |
| Multi-calendar | — | ✅ Native |
| Accounting / reporting | ⚠️ Partial | ⚠️ Partial |
| Revenue management | — | ⚠️ Partial |
Scores by dimension
| Dimension | Chekin | RoomRaccoon |
|---|---|---|
| Ease of use | 7/10 | 7/10 |
| Features depth | 7/10 | 7/10 |
| Value for money | 8/10 🏆 | 6/10 |
| Support | 7/10 🏆 | 5/10 |
| AI capability | 5/10 | 5/10 |
| Scalability | 7/10 🏆 | 6/10 |
| Learning curve | 6/10 | 7/10 🏆 |
| Pricing transparency | 7/10 | 7/10 |
Where Chekin wins
- Value for money — 8/10 vs 6/10
- Support — 7/10 vs 5/10
Where RoomRaccoon wins
- Channel manager — native in RoomRaccoon, not in Chekin
- Multi-calendar — native in RoomRaccoon, 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 RoomRaccoon if: Small independent hotels and B&Bs in Europe or South Africa wanting PMS + channel manager + booking engine + payment processing in one subscription.
Pick by operator profile
| Profile | Winner | Why |
|---|---|---|
| Solo host (1-5 units) | Chekin | Higher profile fit (6.8 vs 6.4). |
| Boutique operator (6-20 units) | Chekin | Higher profile fit (7.2 vs 6.6). |
| Professional PM (20+ units) | Chekin | Higher profile fit (7.3 vs 6.6). |
| Enterprise (100+ units) | Chekin | Higher profile fit (7.2 vs 6.5). |
| Multi-market operator | Chekin | Higher profile fit (7.2 vs 6.7). |
| Tech-forward, AI-first | Tie | Both score within a rounding error on this profile — pick on pricing and gut. |
| Budget-conscious | Chekin | Higher profile fit (7.4 vs 6.6). |
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 →
RoomRaccoon in one paragraph
RoomRaccoon — All-in-one hotel management system for small independent hotels and B&Bs. Strengths: All-in-one bundle is legitimately unified — PMS, channel manager, booking engine, payments; Strong presence in European independent-hotel and B&B segment; Called ‘the Rolls Royce of PMS systems’ by multiple positive reviews. Weaknesses: Users cite “a lot of flaws they are still working on” — product maturity gaps persist; Frequent system bugs and slow customer support cited consistently. Full RoomRaccoon review →
See also
- All Property Management Software comparisons
- 5stelle vs Chekin
- 5stelle vs RoomRaccoon
- AirDNA vs Chekin
- AirDNA vs RoomRaccoon
- Amenitiz vs Chekin
- Amenitiz vs RoomRaccoon
FAQ
Is Chekin or RoomRaccoon cheaper?
Chekin is cheaper at the entry level ($4/mo vs $188/mo).
Does Chekin have better AI than RoomRaccoon?
Chekin and RoomRaccoon score equally on ai capability (5/10).
Which is easier to use, Chekin or RoomRaccoon?
Chekin and RoomRaccoon score equally on ease of use (7/10).
Can I switch from Chekin to RoomRaccoon?
Yes, but plan for migration cost: channel reconnections, template rebuilds, automation recreation, and team retraining. Both Chekin and RoomRaccoon export reservation history; neither exports their automation rules cleanly. Run both in parallel for at least two weeks before cutting over.