Vintage Vacations

A hobby turned thriving glamping business on the Isle of Wight.

Airstream trailer with deckchairs

Helen and Frazer Cunningham were among the UK’s glamping pioneers when they started letting their Airstream trailer in 2004. In this, their 16th season, the couple’s fleet now numbers 18 but their seasonal offering remains true to its roots, with a real vintage atmosphere and “a healthy dose of kitsch”. We talk to Helen.

What’s your back story – your life before glamping?
What started out as a hobby turned into a life-changing business. We bought our first 1965 ‘Tradewind’ Airstream over from America in early 2004. Having a holiday home on the Isle of Wight, it made sense for us to keep it on the island. The original idea was to use it ourselves and maybe rent it out for the occasional holiday and photoshoot. However, once we had our hands on our ‘trailer’ we really caught the bug and had a ‘what if…’ vision for a whole field of retro caravans.

Our first local newsagent advertisement caught the eye of a travel editor from The Guardian newspaper who came to stay and gave us a great review, bringing in our first spate of bookings. Word spread during 2004 and we were thrilled to find that so many others loved the idea of a stay in a vintage caravan. We made the move to the Island full time in 2007 and 2020 will see our 17th season! With 13 American vintage caravans, as well as our various British classic caravans, we have 18 in the fleet now.

We are very proud to have been among the very first businesses offering glamping holidays in the UK and the original glamping holiday operators on the Isle of Wight!

As Vintage Vacations became our full time jobs (our previous 25 year careers were in the photographic industry), we added to our holiday locations with The Mission, The Scout Hall and The Shack. We also ‘curate’ The Bungalow. We are always on the lookout for interesting places and never quite know what our next project will be (well, we do actually… Tiny Homes Holidays –

We put our hearts into all of our projects – we do what we love ourselves and hope that guests will love it too. We like to think our places are low on twee and high on real ‘vintage’ atmosphere, with a healthy dose of kitsch to stop it all getting too serious.

Location of Vintage Vacation's site

How did you research the business before entering it?
We did zero research – we just bought an old caravan and stated renting it out. We had literally no idea it would turn into a life-changing business!

Tell us about your location and site
One of the biggest challenges was finding a home for the business and it took six years to get planning permission. We have been at our current site at Hazelgrove Farm for 12 years. When we originally started we were simply some vintage caravans in a farmer’s field, and to be honest we haven’t really changed the business model. We like to keep things really simple and let the vans speak for themselves.

How did you tackle getting planning?
We had to employ specialist planning consultants – it cost us thousands of pounds and one failed application on a piece of land that we bought. We were advised that the land was suitable but had not foreseen the vitriolic local objections! This was 13 years ago when little was understood about niche tourism. The land is now home to Tiny Homes Holidays, which again faced objections but was approved by planning committee.

Vintage table lay out with cards and teacups

How did you finance the project?
For Vintage Vacations we had a DEFRA grant of £12K that we had, of course, to match with our own funds. Our landlady was also able to benefit with a tag along grant for development of her own small farm enterprises.

How did you work out your brand and how do you publicise yourself?
Vintage Vacations was a lightbulb idea that just happened at the right time and grew like a snowball with us hanging on to it! Because we were doing something really new our press coverage grew organically. It was the first review (by an Observer journalist who was one of the first people to stay) that really kickstarted the business. We have always had quite a strict policy regarding the press that we liaise with – only high end.

We are always amazed by and grateful for the continued press interest. It really was a case of a good idea at the right time. We do not send out press releases but we do send out updates to our local destination marketing organisation (DMO), Visit Isle of Wight, which has a wonderful press department for which we are grateful and happy to pay our destination business improvement district (DBID) contributions to.

Vintage vacations plan in diary

How would you describe your ethos and unique selling point?
Our ethos is to provide a fun and stylish glamping break. We never ‘over sell’ what we offer – again the Airstreams speak for themselves!

How did you choose your interior decoration?
The Airstreams are so iconic we wanted to keep them as original as possible. We have always loved vintage, and after having worked as a photographic stylist for 20 years, I had amassed a vast collection of ‘props’ that all found good homes!

We decided to gently restore our vans rather than rip them out completely. Call us old romantics but we feel that this keeps the ‘soul’ of the caravan and continues the tradition of many happy holidays past. What this means is that if the original Formica and door handles (for example) are a bit worn but still working perfectly well we will leave them intact, but things like cookers, soft furnishings, beds etc. are replaced with sympathetic alternatives. Vintage fabrics and accessories are used where we are able.

Onboard facilities include fridges, cookers, heaters, toasters, and CD radios. Lots of kitchen equipment is provided as are towels and fresh white linen. We also have a stock of vintage board games and classic CDs.

All of the American vans have onboard showers and there is a toilet facility on site not far away (guests can also hire a chemical loo). The British vans do not have onboard hot water or showers and are priced for a fun budget break.

Each caravan has it’s own brightly painted picnic bench, parasol, classic deckchairs, barbeque and log burner.

Interior style inside the airstream trailer

What challenges have you faced?
Weather, maintenance of vintage caravans, growing competition, weather, finding a home, weather… but after 16 years we have most of this nailed (apart from the weather).

What are your plans for next season?
We will be revamping some of the vans (we always do winter revamps) and we already have a few weddings, group bookings and holiday bookings in place – we feel 2020 will be a strong year! We have also started a new off-shoot business providing curated holidays for women ( in which Vintage Vacations will play a strong role.

Describe your average day mid-season
LOL! If you look on my Instagram for ‘vintagevacations’ you will see a day in my life story. We run three businesses (to be four when Wyldesistas launches on 3 November) so I am constantly spinning plates. The biggest learning curve for me over the last three years has been learning to delegate. We are lucky to have some fantastic people working for us.

On site at Vintage Vacations a day would consist of sorting out the day’s bookings and liaising with new bookings, answering enquiries, organising staff and changeovers for vans, cleaning the toilet block, maintenance and grass mowing (it’s a big field!). Maybe putting up one of our vintage pop up vans that acts as extra bedrooms, or a tent… or even our vintage marquee that is hired out for group bookings. Then there is book keeping, booking ferries for guests and dealing with our various accounts for linen, cleaning materials and waste management. We also greet every guest personally to show them around their Airstream accommodation.

Vintage radio inside the trailer

Do you enjoy the business?
Yes! I still get bowled over by the beauty of the Airstreams every day as I drive onto the field. We get really lovely guests and that interaction is one of the nicest aspects of the job. I also really enjoy the styling and preparing of the vans for guests.

What are you most proud of?
Having a good idea and not being afraid to go for it. If we had a pound for everyone who said to us “I thought of doing that” we’d be very wealthy!

We are also delighted with our accolades. We received a ‘Highly Commended’ award at the IOW Chamber of Commerce Business Awards for Excellence in 2009 and were floored to actually win an award in 2010 in the Tourism & Leisure category. 2012 saw us as runners up in Coast Magazine’s awards (Best Caravan and Camping Site). The Shack won Cosiest Cottage Hideaway in the 2013 My Isle of Wight Awards, and in 2014 and 2015 we picked up two further My Isle of Wight Awards for the Best Place to go Glamping for the airstreams.

What other outdoor hospitality sectors do you operate in?
While glamping is our first love, we have now taken the glamping vibe to the next level with our Tiny Homes Holidays. By this I mean we have created permanent structures with nothing temporary or ‘camping’ about them, open all year and with an on-site studio for workshops and retreats. We also have a beachside shack, a converted tin tabernacle and a converted Scout hall – these heritage buildings have been an essential source of winter income alongside the seasonal glamping business.

Decorations from inside the trailer

What advice could you give to someone coming into the industry?
Honestly? Do not be a “me too” – glamping is now an established industry and you have to be original. It’s not easy money and it’s hard work! Another option would be to buy an existing glamping business that is thriving and take it to a new lease of life with your own unique viewpoint. Vintage Vacations is for sale! (

One other thing I would like to add about running a glamping business. Depending on your stage of life, running a seasonal business has superb advantages. The main one being that you can work like mad for seven months of the year and have a two or three month long ‘holiday’. If, like us, you are bitten by the wanderlust bug this is a major advantage!

Dining space within Airstream trailer


Imported from the USA

Eves Tipis

Canopy & Stars
One Off Places



Vintage Vacations
Hazelgrove Farm
Ashey, Ryde
Isle of Wight, PO33 4BD

07802 758113

About Open Air Business 1380 Articles
The voice of outdoor hospitality - in print and online. If you liked this article, subscribe to the printed magazine here. We produce industry e-news between issues - please sign up here