The 2026–27 season opens as a single choice between two climates — whale season in Los Cabos or first lifts in Courchevel — booked on the same clock, and earlier than ever.
Luxury winter travel now divides into two parallel seasons booked as one decision: sun villas led by Turks & Caicos and Los Cabos, ranked second and sixth on Haute Retreats’ Billionaire Villa Index, and catered chalets from Courchevel 1850 to Zermatt. Peak alpine weeks require twelve to eighteen months’ notice; Los Cabos holiday weeks, nine to twelve — and both are being decided in September.
Two mornings, one household. In the first, the terrace faces the Pacific and the coffee arrives as a grey whale surfaces a few hundred yards offshore, unhurried, on its way south. In the second, the same family — same chef, same manager, same rhythm to the day — is at 1,850 meters watching the first lift of the morning start its climb through the pines above Courchevel. The luxury winter has become a choice between two temperatures, and both are being decided now.
With the official opening of its 2026–27 season, Haute Retreats — the luxury villa rental and private concierge company with more than 2,400 fully staffed estates across 83-plus destinations — is presenting winter the way its guests have started to book it: not as a list of destinations but as two parallel winters. One is warm, anchored by Turks & Caicos and Los Cabos, second and sixth on the company’s 2026 Billionaire Villa Index. One is alpine, running from Courchevel 1850 through Val d’Isère, Verbier and Zermatt. The households are interchangeable; the weather is the decision.
What unites the two is the calendar. Interest in the company’s chalet pages rose roughly fivefold in a single month this September, according to its own tracking, and its published guidance puts peak alpine weeks at twelve to eighteen months’ notice and Los Cabos holiday weeks at nine to twelve. Whichever winter a family prefers, the version of it worth having is chosen in the fall.
The sun season has a newer headline than the Caribbean this year, and it sits on the Pacific. Across its Haute Retreats Los Cabos villas — five enclaves running from Palmilla and Pedregal to San José del Cabo and the Tourist Corridor — winter is the market’s defining stretch. From December to April the air is dry, the afternoons hold in the high seventies, and the grey whales that summered in the Arctic arrive to calve in the lagoons up the coast, passing the terraces on their way. The company’s guidance for the holiday weeks is nine to twelve months ahead.
Sixth place on the index makes Los Cabos the highest-ranked winter market that most of the company’s Caribbean-loyal guests have never tried — which, in a season where Turks & Caicos at second place absorbs demand months in advance, is precisely its argument. The flight logic helps: for the American West, Los Cabos is the shortest route to a fully staffed winter there is.
The alpine half needs less introduction and more punctuality. Courchevel 1850 remains the address most travelers name first, with Val d’Isère and Méribel alongside in the French Alps and Verbier, Zermatt and Klosters across the Swiss collection. The chalets are built around the way the fortnight actually unfolds — spas for the afternoon the legs give out, cinema rooms for the evening the children stay in, wine caves for the dinner that lengthens — and the resident team has already handled the lift passes, the instructors and the boot fittings by the time anyone thinks to ask.
The company’s published guidance for Christmas, New Year and February is twelve to eighteen months, and the finest catered chalets are re-booked by the same families before the previous season’s snow has gone. The September surge in chalet interest suggests the market has finally taken the mountain at its word.
Behind both winters runs one standard, and it is what makes the pairing possible. Three weeks before any arrival, whichever climate, the household is briefed on the specific family it will receive — who eats what, who sleeps where, which evenings are occasions. A chef is chosen to fit that brief rather than pulled from a schedule, the provisioning is placed in advance against supply chains that tighten at peak, and a concierge desk sits above the whole household for everything beyond the property line. The family is described once, and the standard travels — which is the reason two winters can be booked as one decision.
“Winter is the season where our guests stop choosing a destination and start choosing a temperature. Los Cabos in January and Courchevel in February are the same holiday under a different sky. The only mistake we see families make is assuming the warm half of that choice can be made later than the cold half. Increasingly, it cannot.”
— Sabrina Piccinin, Founder and CEO, Haute Retreats.
The two winters now close on converging schedules, and the fully staffed layer — a minority of inventory in both climates — closes first. For travelers deciding between sun and snow, the practical answer suggested by the company’s own calendar is the least romantic one available: the choice itself can wait until the first lift or the first whale; the booking cannot. Both winters are open now through the Haute Retreats concierge.
About Haute Retreats
Founded in 2016, Haute Retreats is a luxury villa rental and private concierge company representing more than 2,400 fully staffed private estates across 83-plus destinations worldwide, with end-to-end service including private chefs, villa managers, drivers, yacht arrangements and bespoke experiences. The company is ASTA-accredited, a three-time Luxury Lifestyle Awards Winner (2024–2026) and a 2026 Condé Nast Traveler Readers’ Choice Nominee. Haute Retreats holds a 5.0 rating on Trustpilot, and 80% of its guest families return.
