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Our story

Sierra Retreats is a luxury bespoke holiday accommodation booking agency offering additional concierge services. 'Sierra' referring to jagged mountain range and 'Retreats' to escape, we create and design the perfect unique holiday for you in those sought-after destinations. 

Founder and CEO Joshua Todd working closely with his partner Cassandra striving for perfection. Both with years of extensive hospitality and personal care experience, both very well-travelled and cultured bringing the very best service. 

The idea to start Sierra Retreats is to offer a distinctive professional service to clients that want a hassle-free holiday. Joshua has been a private chef for over 15 years previously at Blenheim Palace for the Duke & Duchess of Marlborough, before working for very affluent UHNW guests in luxury homes, estates, chalets, villas and onboard private yachts. Before this he has gained great knowledge in Michelin starred and other high-end establishments. 


The early part of this journey started in a chalet in Baqueira, Spain (the hidden gem as we refer to it) where Joshua knew he would return to one day. Setting up here is the starting point of much more to come for Sierra Retreats. 


Our HQ is currently based in the UK, Shropshire. Joshua and Cassandra run and manage the company as well as the day to day operations, searching for perfection and directing the business forward. Personally, selecting and visiting the accommodation featured, we can give our recommendations and expertise.

We have spent many years exploring and travelling the world from some of the most remote islands to the liveliest cities, taking part in many excursions and activities. We understand the importance and the aspects that make a great holiday. Our aim and statement 'Unique Luxury Getaways' is a combination of visiting a desirable undiscovered destination, our bespoke luxury service and exclusive touch. It will be a holiday you will remember for a life time.

With Joshua leading the business and team he really understands the importance of what our clients, their friends and families want to experience. Making sure that from enquiring, to after your holiday you are satisfied above and beyond expectations. 

We will go out of our way to give you a faultless service, ensuring all your needs are fulfilled, booking your every requirement.

Meet the team


Joshua Todd - Founder & CEO

Owner & founder of Sierra Retreats, Josh has spent many years as a highly trained private chef, previously working in chalets and private homes globally. With his love for travel and wealth of experience in luxury hospitality the concept for Sierra Retreats was formed. He is dedicated to making sure every client experiences their holiday of a lifetime.

Cassandra Jennings - Marketing & Design

Cassie has a keen eye for detail and with a strong background in luxury travel she truly knows what it takes to design bespoke holidays. She is a very well cultured and family person, she understands the importance of ensuring all ages and walks of life receive what they deserve. Her finishing touches to the business are what makes us unique.


Joanne Boyd - Admin & Sales

Highly experienced in customer service and organisation, Jo is key for helping our clients feel at ease when looking to travel with us. She has a big passion for travel and luxury and she is on hand to answer and reply to any questions you may have, from holiday enquiries to excursion bookings.

Lucas Coombs - Camera Operator 

An expert in visual arts and an incredible photographer, Lucas has travelled far and wide to capture unique luxury getaways. We've put him through his paces, capturing real moments like hanging on to the back of a snowmobile with a camera in hand. Lucas is available to photograph and capture those very special memories made with family and friends while enjoying a holiday with us.


Aidan Willis - Social Media & Web Development

Aidan plays very important role with us keeping our clients up to date with the current trends, best places to visit at certain times of the year and the incredible accommodation we have to offer. He is running our social media platforms showcasing some of the most unique places. He also has some fresh ideas and input having not long come out of university with a business degree.

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