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Sykes Cottages

Housekeeping Supervisor

Weymouth Full-Time 23810 - 25000 £ / year (est.) No home office possible

Join the dream team at Dream Cottages

Salary: £23,810–£25,000 per annum
Hours: 37.5 per week, 9am–5.30pm, 5 days over 7 (including Fri & Sat) – some on-call duties may apply
Location: Weymouth Office, Dorset

About the Role

We’re looking for a Local Supplier Lead to join our Weymouth team. You’ll manage properties, support housekeepers, liaise with owners, and make sure every guest has a flawless stay. During busy times, you’ll also jump in with the Managed Service Team to keep everything running smoothly.

What You’ll Do

Build and maintain strong relationships with cleaners, suppliers, and property owners
Recruit, train, and manage self-employed housekeepers and maintenance contractors
Ensure properties are cleaned and maintained to standard, conducting visits as needed
Support the Property Services HUB and assist with cleaning or maintenance when required
Monitor performance, provide feedback, and act on NPS results for continuous improvement
Participate in the out-of-hours emergency callout rota as needed

If you’re organised, proactive, and love giving great service, this role is for you!

What You’ll Bring

Full UK driving licence
Strong customer service skills
Basic property maintenance/DIY knowledge
Excellent negotiation, problem-solving, and organisational skills
Contractor management experience and ability to build strong relationships
IT literate – confident with MS Office and internal databases

Bonus points if you’ve got holiday let or hospitality experience, know the local area well, and have experience seeing work orders through from start to finish.

Who Are Dream Cottages?

We’re Dorset’s leading holiday cottage provider, managing over 500 stunning coastal and countryside properties. As part of Sykes Holiday Cottages, we help guests make unforgettable memories while supporting owners with expert local and national marketing. We love creating amazing holidays, supporting our team, and making a positive impact on people and the planet.

Why You’ll Love Working With Us

At Dream Cottages & Sykes, we believe in doing right by our people:

Performance bonus – up to 5% of salary
33 days holiday (including bank hols) + extra days with long service
Your birthday off just because!
Two paid volunteering days each year
Proud to be a BCorp – we care about people & planet
Enhanced Maternity & Paternity leave (24 weeks maternity, 3 weeks paternity at 100% pay)
Generous discounts on stays for you, family & friends
Employee savings scheme
24/7 mental health support and health cash plan
Loads of training & development opportunities

We’re all about diversity, inclusion, and bringing your authentic self to work. Need adjustments for the recruitment process? Just ask, our team is happy to help.

Ready to lead our local housekeeping team and make every guest stay perfect? Apply now!

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Housekeeping Supervisor employer: Sykes Cottages

Dream Cottages, part of Sykes Holiday Cottages, is an exceptional employer located in the picturesque Weymouth area, offering a vibrant work culture that prioritises employee wellbeing and development. With generous benefits such as a company-wide bonus scheme, extensive annual leave, and a commitment to diversity and inclusion, we empower our team members to thrive both personally and professionally while contributing to the satisfaction of our guests in the beautiful Dorset region.