Trulli Puglia, Italy

Give traditional villas the boot and head to Puglia, Italy’s southern heel, where clusters of conical-roofed, whitewashed houses sprout like mushrooms from the ground. You’ll find traditional trulli spread across the Bari, Brindisi and Taranto provinces, but the most extensive concentration can be found in Monti, Alberobello, where over a thousand huddle together.

Archaeological discoveries in the region can date the Pugliese domiciles back to the Stone Age, but the most common tale told to explain their existence takes root in the 14th century. Land legislation dictated that any area with liveable dwellings would be subject to tax, so skilled stonemasons created trulli in a fashion that meant they could be dismantled with the removal of a single brick. Despite this collapsible quality, the dry-stone structures are incredibly durable, many lasting for hundreds of years.

Most comprise three to four bedrooms (sleeping four to six) with communal dining areas beneath the domed roof. Family and friends will enjoy the social aspect created by the central space and interconnecting rooms. Nicholas and Sarah, the owners of Trulli Italy trulliitalyinpuglia.com moved to Puglia in 2005 to renovate their own trullo, and have since extended their portfolio significantly. Visiting in November offers guests the chance to roll up their sleeves and help with the olive harvest and first pressing of the oil using a traditional stone press. With a similar wealth of local knowledge, Trulli Online has been inviting guests to experience its beautiful collection of individually owned trulli for over 15 years. Best for groups is Borgo Specchiaruzzo, accommodating up to 14 guests across six bedrooms. Renting a car will give you the freedom to explore the winding country lanes, perfumed by the heady scent of citrus groves; public transport is sparse.

Trulli are best suited to self-catering, allowing guests to make the most of an abundance of local produce. Stock up on essentials at Ostuni’s Saturday market, a 20-minute drive away. Back at base, the fairy-lit garden demands that dinner be taken alfresco. Load the table with plates of orecchiette pasta smothered in a cime di rapa sauce before raising glasses to the good fortune that brought you here. Saluti!

Riads Morocco

Even the most highly skilled navigators will find their maps useless in a Moroccan medina, as the maze of narrow corridors, rows of textile merchants and towering walls conspire to confuse. Uniform Moroccan homes huddle side by side to form this intricate medina web, as historically riads were built adjoining on three sides without exterior windows and only identifiable through heavy cedar doors. Building skywards as opposed to outwards helped increase a family’s privacy in areas where buildable land was scarce. In contrast to the nondescript exterior, once inside a riad you are transported to a vibrant oasis filled with palms, citrus trees and colourful zeliji tiles. ‘Riad’ translates to ‘garden’ in Arabic, with a lush space forming the central hub of nearly every home, the many rooms leading off from it. The open-plan layout lends itself to grand group getaways.

A recent boom in tourism to Moroccan has seen a flurry of dilapidated 18th- and 19th- century riads revamped as intimate guesthouses, such as the elegant Dar Hanane dar-hanane.com by Pure Riads in Marrakech. Fierce competition exists between riad owners, which has helped keep prices low: even some of the most luxurious cost less than basic hotel accommodation in European capitals. Hotel and Ryads manages an excellent range of properties. Our pick is Riad Cinnamon, in an old merchant’s house. Walls are decorated in regal navy and vibrant turquoise, bathrooms are dripping in gold and the dipping pool is the ideal place to refresh while sipping on fresh mint tea. Marrakech may have the monopoly with over 800 riads (and rising) but Hotel and Ryads also offers outposts in Fez, Essaouira and Casablanca. Morocco is not the place to go self-catering. Meals are inexpensive here and Riad Cinnamon comes with its own kitchen staff and charges around £5pp per meal. Tagine is the speciality. The huge conical earthenware pots are laden with rough-cut beef or lamb, preserved lemons, ghee, saffron, fenugreek and saffron before being taken to the local hammam to make use of its farnatchi (wood fire), where the tagine is placed in the embers to cook for six hours. The staff then bring it back to the riad for the grand reveal, set on a beautifully laid dining table .

Trailer Parks USA

In the 1930s, ‘trailering’ became a popular pastime in the US thanks to Wallace Merle Byam, inventor of the Airstream, whose silver bullet appearance is as synonymous with road tripping as a Bruce Springsteen album on the car stereo. Byam built the original trailer for his wife so she didn’t have to sleep on the ground. Initially, he attached a tent to a Model T chassis, but later swapped out the canvas for an aluminium shelter, adding a stove. Et voilà: a new travel trend was born. If, like Wally’s wife, you are less than happy with roughing it and prefer a smattering of mod cons to be within arm’s reach, then America’s new wave of chic trailer parks are just the ticket. Unlike Byam’s early design, two people can comfortably sleep in the modern Airstreams and most come with double beds, good showers and kitchenettes.

One of the best examples of the classy trailer park genre is in Marfa, Texas, (population 2,121). Open since 2006, El Cosmico has seven refurbished vintage trailers, three tepees, and eight safari tents, each sleeping two. Hiring of the whole site is possible, with room for scores of pop-up tents on the 7ha grounds, plus 30 extra tents available to hire. Opt to stay in bright blue Vagabond, or Imperial Mansion (Beyoncé once bedded down here) with its woollen pillows handmade in Bolivia, private outdoor shower and a patio for dozing in hammocks, stargazing and practising the sweet art of doing nothing. Once you tire of that, borrow a bike to cycle into Marfa. The desert town has a long history of inspiring bohemians, artists and the odd cowboy with its Wild West landscape. While there, visit La Mansana de Chinati juddfoundation.org – the original workspace of the great minimalist artist Donald Judd. The town’s influence is so widespread that hip hotel brand Ace has called upon its retro aesthetic for inspiration in shaping its own identity. Fancy something sleeker? In the heart of California’s Sonoma wine country, spa-inspired bathrooms, boutique hotel bedding and pinot packages for sipping round the campfire come as standard at Autocamp. It’s suitable
for between five and 130 and cook-outs using top-notch local beef are a speciality.

Castles UK

Once upon a time, legend saw fair maidens rescued from castle towers by chivalrous knights, monarchs would escape the heat of battle as castles were won and lost in a landgrab spanning centuries. As war became less frequent, the castle became a symbol of status and wealth; lord, ladies, counts and countesses commissioned their own. After both World Wars, many of these castles were left in ruins, and by the 1960s an average of two per week were being torn down across the UK due to the staggering cost of upkeep. Thankfully, many survived and have been repurposed into sumptuous lodgings fit for royalty. Gather your knights and take over your own fortress – even the smallest sleep at least 30 noblemen and women.

Among the 90 properties in its portfolio, Celtic Castles boasts one that was recorded in the Domesday Book. Amberley Castle played host to a revolving door of royalty throughout its 900-year history, including Elizabeth I, Queen Elizabeth II and Henry VIII, who came here seeking divorce counsel, before offering its servicesas a plush rentable residence. Known locally as the ‘Pearl of Sussex’, its working portcullis is lowered daily at sunset. Catering is perfect for parties, with the Queen’s Room restaurant available for exclusive use for 56 guests.

A typical five-course menu might feature mackerel served with wasabi, apple, cucumber and yuzu, followed by local beef and, at this time of year, Jersey Royals.

Augill Castle, meanwhile, was built in 1841 by John Bagot Pearson to overshadow his brother’s own house further down the hill. The result? A majestic vision of a medieval castle equipped

with turrets, towers and intricate lattice windows. Current custodians Simon and Wendy Bennett rescued the dilapidated castle in the hopes of turning it into a family home. Nowadays, the 17-bedroom residence hosts raucous dinner parties followed by banquet-style breakfasts. The baronial dining room features an Italian-style menu featuring a majority of ingredients sourced within a few milesof the castle. Cumbria meets Umbria with slow-cooked lamb ragù It’s rounded off with an excellent selection
of British cheeses and molten chocolate pudding.

Windmills Worldwide

Historically, windmills were developed to mechanise water-pumping and grinding cereals, with the first known design emerging in Persia in 900AD. By the 14th century, they were used to harness wind power all over the world, easing the production of everything from paper and paint to gin and mustard. Post-Industrial Revolution, however, and overtaken by the growing number of coal-powered factories, many mills were left to rack and ruin. Host Unusual puts the wind back into the sails with its collection of 16 wind and water mills that have been refashioned as quirky group lodgings. The self-catering accommodation suits both smaller groups and multi- generational families given the ample interior space, cosy circular dens found at the top of towers and secluded countryside where the majority of mills are found.

Of the 70 or so windmills scattered across the Cyclades, the sherbet-hued Santorini Windmill Villas are among the most attractive. A world away from the selfie-stick- wielding crowds of Oia, the three mills that each sleep five are perfectly positioned between the capital of Fira and the whitewashed village. A breeze cools during the scorching summer months and at sunrise the windmills are bathed in dusty pink. Start with the complimentary local fruit basket before firing up the barbecue. Closer to home, in the heart of the Welsh countryside, Llancayo Windmill (sleeping 12) was built in 1813 as a grain- grinding mill and destroyed in a fire 17 years later. The eyesore stood as a blight on the horizon until purchased by a developer in the late 1990s. After an extensive restoration project, the doors were flung open in 2010.

The five-storey windmill (sleeping five) adopts an industrial feel with exposed wooden beams, stark white walls and wrought-iron fittings. Two of the bedrooms are located within the tower itself and the remaining four in the adjoining cottage. Step outside the front door, cross the corn fields and followthe river down to the market town of Usk, where you’ll find a cluster of friendly pubs – try the Nag’s Head nagsheadusk. co.uk for its hearty lamb pies. Serious ramblers should seek out the trails of the Black Mountains, just an hour’s drive away, while keen fishermen can purchase a fly-fishing licence from Sweet’s the fishing shop before tackling the River Usk

Châteaux France

These can be found all over France, but the highest concentration is in the Loire Valley, where the royal court was established during the Renaissance. The valley was as much a strategic choice as it was an aesthetic one: in addition to the emerald-green hillside, it was then a thriving trade route. Eager to celebrate his victories at the end of the Hundred Years’ War, King Francis I had a series of châteaux built to represent each of his triumphant battles. The love affair with these pleasure palaces was, however, short-lived as by the 17th century French royalty had retreated back to Paris. Breathing a new lease of life

into relics of the past, 21st-century owners offer large parties the chance to occupy these grand homes.

Visiting in shoulder season (May and September) ensures prices are favourable, leaving more gold in your purse to spend on the finer things. Château Charme du Bois is straight out of a dream. Your own royal court will sleep comfortably in its six bedrooms, most of which are en-suite and stocked with plush linens . Just 20km away lies Brive-la-Gaillarde, one of France’s prettiest towns and home to a lively truffle trade. Fill the fridge at the thrice- weekly market (Tuesdays, Thursdays and Saturdays) held at Place du 14 Juillet. Or, a private chef with a Michelin background can be arranged. For a Mediterranean
option, explore family-run South France Villa’s portfolio. With a music room, well-
appointed rooms, and a pool, Château du Beau Parc can fill endless summer days. Given
its perch between the tranquil town of Pézenas and the fishing port of Cap d’Agde, we
suggest a seafood supper at Les Trésors de la Mer 00 33 660 59 70 17 which will save
doing the washing up later.