About Helpful Holidays

Experience the magic of the South West with Helpful Holidays

At Helpful Holidays, we believe the South West is one of the most fabulous holiday destinations in the country. Based in the heart of the region, we offer over 1000 self-catering holiday homes, in locations varying from rugged moorland to stunning cliff tops, and everything in between!

Where We Operate

We offer properties across:

- Devon

- Somerset

- Dorset

- Cornwall

Helpful Holidays’ Story

Founded over 40 years ago on Dartmoor in Devon, Helpful Holidays began with a simple mission: to make sure guests have happy holidays! By being honest, straightforward and always delivering, and with industry-leading standards of quality, Helpful Holidays has gone from strength to strength. We are proud to have the faithful support of a loyal fanbase of long-standing owners and repeat guests, who holiday with us every year.

Today, we market over 1000 holiday homes, ranging from cosy rural cottages with woodburning stoves, to contemporary coastal houses dotted along either the North or South Devon coastline. With accommodation for all party sizes, needs and requirements, guests looking to explore the South West need look no further than our portfolio for inspiration.

Why Choose Helpful Holidays?

We are more than simply a booking agent

At Chagford-based Helpful Holidays, we are proud to be just that… helpful. We are passionate about the area and the offering we provide; we will do our utmost to ensure your holiday is everything you planned and more. We even have a 24/7 helpline, meaning we are always available to offer emergency support, should the need arise.

A winning combination

We believe the offering we provide our homeowners with is a fantastic solution for those looking to let their holiday homes. We benefit from a large annual marketing budget, not to mention the expertise of our national parent company Sykes Holiday Cottages, from data analysts to legal specialists, they ensure we stay ‘ahead of the curve’ in a competitive and fast-paced market. But crucially, that’s not all. Owners also benefit from the expertise of our Chagford-based team, who have accrued over 40 years’ experience and know all there is to know about letting in the region. We can support with arranging cleaning and caretakers, laundry, pricing, booking optimisation and more.

Meet the Helpful Holidays Team

Our passionate team of 12 are based in Chagford on Dartmoor. From your first enquiry to the moment you check out, we’re here to make your stay seamless and memorable.

“As a close knit team within this fabulous Dartmoor community, we are exceptionally proud of the work we do, and the reputation we have forged. We work incredibly hard to ensure our guests and holiday home owners are happy, and that their expectations are met or exceeded. Of course, we all feel very lucky to live in such a picturesque and varied region… it makes our job a lot easier. Visitors tend to fall in love with the area, just as we have!” — James Webb, Owner Success Manager.

Part of the Forge Holiday Group

Helpful Holidays is proud to be part of the Forge Holiday Group — a group of trusted UK travel brands committed to quality, sustainability and exceptional guest experiences.

Helpful Holidays’ Impact Mission

Helpful Holidays is committed to creating lasting holiday memories with a positive social and environmental impact.

As part of our Impact mission, we aim to:

- Reduce our carbon emissions by at least 50% by 2030 – and reach Net Zero as soon as possible before 2050

- Inspire and enable 100% of our team to volunteer every year

- Positively impact at least 10 community and charity initiatives

As a certified B Corp, Sykes Holiday Cottages is committed to operating with purpose beyond profit. As such, at Helpful Holidays, we're proud to be part of this mission, consistently working to create a meaningful impact on our community, the environment, and the people around us. Our efforts take many forms, including staff volunteering and regular community outreach initiatives in partnership with local schools and charitable organisations.

Read the impact section of our blog for more information. 

Become part of the Helpful Holidays story

If you have a holiday home that you are interested in letting or would like advice on investing in a South West holiday home, visit our Let Your Cottage page to order a free copy of our Owners Guide, or email pno@helpfulholidays.co.uk.

Get in Touch

Have a question or need help finding the perfect cottage? Contact our team of travel experts today!

Email us at help@helpfulholidays.co.uk 

Call us on 01647 401799.

Visit our Support Hub.