For those who crave true originality from a holiday, picture-perfect scenery and top-class service (as lovely as those things are) just aren’t enough.
Their chosen retreat must also have something seriously special about it. Maybe it’s been crafted to a bespoke design, it’s secluded in an enchanting, as-yet undiscovered location…
…or maybe it has an intriguing story to tell!
The unusual retreats we’ve featured here aren’t just unique and interesting in their own right. Each one also boasts a compelling behind-the-scenes tale that will add an extra dimension to your break.
What do we mean? Well, they may have welcomed a world-famous celebrity or two, be directly connected with an iconic figure from history, or been designed and built by someone you’d recognise on TV.
Others have been the inspiration for classic works of art or infamous herbal remedies, have superstar owners, or even provided the setting for iconic rock-star gatherings!
Whether or not you’re planning to take a holiday soon, we highly recommend arming yourself with refreshments before browsing this list… because once you dive in, it’ll be devilishly difficult to tear your eyes away – and harder still to choose a favourite tale!
Author: Nina Jervis
Main image: Seaside Retreat, Sussex
Isleornsay, Isle of Skye, Scotland
Rest your weary heads in a dreamy lighthouse cottage, blissfully cast away on a soul-soothing private island off the rugged Isle of Skye.
Eilean Sionnach Lighthouse Cottage has two famous connections. Firstly, when the National Lighthouse Board sold the cottage following the automation of lighthouses its first owner was Gavin Maxwell, author of the book and film ‘Ring of Bright Water.’ The book is about an otter called Mij and the otters we see today around the island are thought to be descended from this famous ancestor. Secondly, the current owner Angel Sedgwick is a relative of the late Edie Sedgwick who was a 60s icon, ‘IT’ girl and thought to be the muse who inspired the invention of the mini skirt as she was the first to be seen and photographed around London hitching her skirts up! She was also Bob Dylan’s girlfriend and features on the cover of his second album. Her cousin Paulita Sedgwick (also a film maker, well known 60s socialite and artist) bought the island in the early eighties for her son, the current owner, Angel. His very own treasure island!
Coolbaun, Tipperary, Ireland
Travel back through time with an ‘over-knight' stay for two in a majestically authentic 16th century Gaelic castle.
An Australian Kennedy genealogist who visited The Black Castle believes that it is one of 6 possible historical connections to JFK's family. The last Kennedy to own the castle in 1641 ish (before Cromwell confiscated the lands etc) was recorded as John Kennedy (along with his brothers, Rory and William) and, as it was traditional to carry the name on through the family line, JFK's family may have hailed from the castle before they moved to New Ross, County Wexford. A spooky aside is that "Tullaun" apparently means "grassy knoll" (which is where some folks believe that JFK was actually shot from).
San Luis Obispo, California, USA
A vividly kitsch, grandly one-of-a-kind resort just off US Route 101, where the good times roll and no two rooms are the same.
Bedrooms: 110 rooms/suites
Sleeps: Varies
A glittering array of celebrities visit this iconic Inn, situated halfway between Los Angeles and San Francisco (Rupert Grint, Malcolm McDowell and Katy Perry to name but a few!). Historically, the founder – Alex Madonna – was a friend of William Randolph Hearst Jr. On the Madonna Inn property, there are a few pieces of décor that were sourced from the Hearst Castle – including the solid marble balustrade which leads upstairs to the Boutique and Gift Shop.
Matlock Bath, Derbyshire, England
An incredible Georgian Grade II-listed former hotel – with two hot tubs and its very own pub! – for larger-than-life group stays in the scenic Derbyshire Dales.
A magnificent Georgian Grade II-listed former hotel – in which Lord Byron himself once stayed, not to mention then-Princess Victoria. The Byron Room is an impressively grand dining room in which Lord Byron once etched a poem on the window-pane!
St. Eval, Cornwall, England
Exquisite architecture, fabulous eco-credentials and sweeping views of countryside and coastline - that's what to expect at Sheepfold and Sheepshed, a pair of eco-barns in glorious North Cornwall.
Bedrooms: 3 (+2)
Sleeps: 8 (+4)
Sheepfold is owned, designed and built by Charlie Luxton, founder of Charlie Luxton Design (https://charlieluxtondesign.com/) and tv presenter of Building the Dream, Homes by the Sea and guest presenter on DIY SOS.
Bury St Edmunds, Suffolk, England
How about an unforgettable escape to the beautiful Suffolk countryside with West Stow Pods, where there's something for everyone at this glamping idyll.
Bedrooms: Varies
Sleeps: Up to 4 per unit
The site of West Stow Pods plays host to an old Scots pine tree, whose iconic roots grow up and out of the ground, creating a maze-like canopy. Locally, these Scots pine roots are known as Peter Pan's Roots. In the mid-1890s, Peter Pan author J. M. Barrie is said to have visited the West Stow school house, just yards away from the West Stow Pods glamping site. Local people say he was visiting a headmistress he was acquainted with at the school and came upon the twisted roots of the Scots pine while walking through the woods. The tree’s magic is even said to have inspired an illustration in the first edition of Peter Pan!
West Wittering, West Sussex, England
A Sussex beachside sanctuary and paean to music history, complete with a hot tub, sauna and bar, for unforgettable Wish You Were Here-inspired group breaks-by-the-sea.
This beachside Sussex sanctuary was once the seaside haven of Steven O’Rourke, long-time manager of the iconic rock band Pink Floyd. O’Rourke hosted legendary gatherings at his (then pink-hued) beachfront bolthole: not only with members of Pink Floyd, but the Rolling Stones and many others.
Launceston, Cornwall, England
Embrace the natural life and get some literary inspiration under clear starry skies, with the scenic backdrop of Cornwall's ‘Peaceful Valley' to keep you company.
Bedrooms: Varies
Sleeps: 2/4/8 per unit
Thomas Hardy spent a lot of time in this area as he met his wife here. The Old Vicarage at Ekopod is specifically written about in his poem The Face at the Casement.
Bethersden, Kent, England
Live your rural dreams with a group getaway on an exclusive, three-acre family-run farm filled with cosy comforts and a ‘secret' hot tub spa in the Garden of England.
Bedrooms: Open plan
Sleeps:
Longberry Farm used to be owned by actor Herbert Lom (best known for his work in the Pink Panther movies) and the washroom building reportedly used to be a studio he used for art.
Tasman, Nelson, New Zealand
You've heard of the old woman who lived in a shoe, but have you ever actually imagined life in a fabulous piece of footwear? Wonder no longer at The Boot, a fairytale B&B on New Zealand's South Island!
Modelled on the Nursery Rhyme 'There was an old woman who lived in a shoe', this whimsical fairytale retreat has drawn visitors from all around the world!
Buckland Abbey, Devon, England
Experience a luxury shepherd's hut break in the great outdoors, with opulent al-fresco accommodation in the Tamar Valley's Area of Outstanding Natural Beauty on the National Trust Buckland Abbey Estate.
Bedrooms: 1 per hut
Sleeps: 2 per hut
Starbed Hideaway's idyllic cabins for couples are tucked away in the 700acre National Trust Buckland Abbey Estate, the former private home of Sir Francis Drake, the famous explorer and Naval commander. Throughout it's history of ownership from monastic times, through seafarers and to present day, the estate has been a place of retreat, away from everyday life, to slow down, immersed in nature. Now in the custodianship of the National Trust this historic Abbey and landscape is a haven for wildlife conservation.
Glastonbury, Somerset, England
Magical eco-friendly holiday adventure in the enchanting E-den cabins in Glastonbury, with breathtaking views towards Glastonbury Tor and the Somerset levels.
Bedrooms: 1
Sleeps: 2 per unit
Over the past years The Middlewick has hosted the royalty of Glastonbury Festival. Mumford and Sons, Kaiser Chiefs, Foals, Self Esteem, Celeste - to name a few. The property is fully booked for Glastonbury Festival for years in advance but you can enjoy it any other time of the year. While there you can take a visit to the festival site - a dairy farm run by the Eavis family all the other days of the year. You can also pop into some of the local Glastonbury music venues where you may just watch a future Glastonbury Festival headliner doing a secret gig. The glamping pods at The Middlewick have been featured on George Clarke's Amazing Space so they have their own celebrity status!
Newcastleton, Scottish Borders, Scotland
An award-winning, architect-designed Alpine chalet with a stargazing hot tub, refreshingly off-grid and beautifully nestled 350 metres above sea level in the scenic Scottish Borders.
In the early 1800's, the shepherd at Singdean (where Alpnhaus is) became famous far and wide for the 'Singdean Plaster' cancer cure. Walter Scott (who started as a shepherd at Hyndlee farm down the road) made a plaster of different herbs from Singdean for external cancers and became famous for it even in America.
Cossington, Somerset, England
Two magnificent Grade II-listed retreats, privately secluded on a historic 22-acre Somerset Levels estate for a family-and-dog-friendly escape filled with captivating stories and fun fresh-air adventure
Cossington Park has been owned by the same family for over 300 years. The families who were custodians of Cossington Park and their relatives are well documented as so many of them made a name for themselves in such occupations as MPs, barristers, church incumbents, yeomen, gentlemen, philanthropists and armed service officers. Examples include: Peter Rigby Wason MP, co-promoter of the 1832 Reform Bill and co-founder of the Reform Club in London • Alan Dowdeswell Graham, founder of ICAN, the UK’s largest charity helping children to communicate • Rear-admiral Cathcart Romer Wason RN, grandfather of the present Owner-Guardian of Cossington Park, Graham Wason
Ashurst, West Sussex, England
An award-winning foodie retreat that combines soothing West Sussex countryside views with baking masterclasses and tempting seasonal produce.
Internationally renowed baker and author, Emmanuel Hadjiandreou has been the tutor for many bread making classes here. He has written 3 books which are published in many languages. He teaches our sourdough classes & many other baking days here. Guests can stay in the ‘Bakers Hut’ and meet him, plus join in on one of the classes to learn to make bread while they are staying! (Check class dates when booking)
Underhill, Gloucestershire, England
A romantic hideaway in the heart of the Wye Valley AONB that’s cocooned in nature, styled with eco-friendly luxury, and completely surrounded by wildlife.
Owl's Nest Hideout sits below the old woodlands of Flora Klickmann, an English journalist, author and editor who was best known for her Flower-Patch series of books of anecdotes, autobiography and nature description. The flower patch at Owl's Nest is a nod to Flora, and the owners used to live in Flora's grandparents house.
Broughton, Hampshire, England
An authentic glamping retreat with three quirky bohemian retreats, restyled for luxurious off-grid comfort in the Hampshire countryside.
Bedrooms: Open plan
Sleeps: 2 per unit
This quirky glampsite is themed on Bruce Springsteen songs, with all units named after characters in his songs. The Magic Rat - Jungleland / Wild Billy’s - Spirit in the Night / Mary’s Place - Mary’s Place. Owner Kate is has been a longtime fan of Bruce forever, and when she lost one of her brothers in 2016 ,The Magic Rat boat was inspired by his favourite song. There are subtle little hints around the site which you’ll spot as a fan. There are even Bruce quotes in the showers, and the site has been visited by the brilliant tribute band “Bruce Juice”!
