Job Description
Job Description:
Property Content & Onboarding Executive - Cheltenham (on-site)
Join our journey
Are you passionate about storytelling, beautiful homes, and the power of words to inspire? Bolthole Retreats is an award-winning, independent holiday cottage company specialising in hand-picked properties across the Cotswolds, Herefordshire, the Forest of Dean and beyond. We’re proud to work with some of the most beautiful homes in the region and to create meaningful, memorable holiday experiences for guests from across the world.
Our business is growing fast, but we stay grounded in what matters: exceptional service, authentic stays, and a personal, local approach. Now, we’re looking for a talented Property Content & Onboarding Executive to help bring our properties, places, and brand to life through compelling content.
The role
We’re looking for an enthusiastic and creative Copywriter to join our growing team based in central Cheltenham. This is a varied, hands-on role that combines creative writing with property onboarding, content management, and client liaison.
You’ll be responsible for crafting engaging, accurate and aspirational property descriptions that capture the unique character of each home and its surrounding area. A key part of the role also involves managing property information within our systems, uploading content, coordinating with homeowners and colleagues, and ensuring listings are complete, accurate, and ready for guests to book.
From perfectly formed shepherd’s huts to stunning eight-bedroom country houses, your work will help guests picture their stay and connect with each property before they arrive.
This role is ideal for someone with strong writing skills, good IT confidence, excellent attention to detail, and an organised approach to managing content and property information.
What you’ll be doing
* Visiting new properties with our photographers and meeting owners to gather information and create engaging property descriptions
* Writing creative, accurate property listings for our website and third-party booking platforms
* Producing welcome packs tailored to each property
* Writing local guidebooks for towns and villages across our regions
* Uploading and maintaining content across booking platforms and internal systems
* Writing blog posts to inspire guests and showcase local knowledge
* Loading new properties across multiple listing sites
* Working closely with property owners, photographers, and internal teams to ensure content is accurate and on brand
* Supporting ad-hoc projects and tasks as the business grows
* Assisting with general office administration when needed
About you
* Exceptional written communication skills with a creative flair and strong attention to detail
* Experience writing creatively in a professional capacity
* Able to write engaging, aspirational copy while remaining factually accurate
* Confident meeting and communicating with property owners in a professional and tactful way
* Self-motivated, quick to learn, and comfortable using your initiative
* A genuine appreciation for interiors, homes, travel, and the holiday lettings market
* Friendly, sociable, and able to work collaboratively as part of a small team
* Comfortable managing multiple pieces of work and meeting deadlines in a fast-paced environment
What you’ll get in return
* A key creative role in a successful, independent company with big ambitions
* An office based in central Cheltenham with onsite parking
* Private medical cover for you and your family
* 30 days holiday (inclusive of bank holidays), increasing after 2 years’ service
* Birthday day leave
* Business performance bonus
* Employee discount
* Company pension scheme
You’ll be joining a supportive, passionate team that cares deeply about quality, creativity, and delivering exceptional experiences for both guests and owners. If you love writing, storytelling, and the idea of helping people discover beautiful places through words, we’d love to hear from you.