The official opening of the winter season spans two climates and one standard: sun villas led by Turks & Caicos and Los Cabos — second and sixth on the Billionaire Villa Index — and catered chalets across the French and Swiss Alps. Haute Retreats has opened its winter 2026–27 portfolio across two climates: sun markets led by Turks & Caicos and Los Cabos, ranked second and sixth on its Billionaire Villa Index, and catered chalets in Courchevel, Val d'Isère, Méribel, Verbier and Zermatt. Peak alpine weeks require twelve to eighteen months' notice; Los Cabos holiday weeks, nine to twelve.
MIAMI, Sept. 15, 2026 /PRNewswire-PRWeb/ -- The 2026–27 winter season is officially open, and this year it opens on two fronts at once.
Haute Retreats, the luxury villa rental and private concierge company with more than 2,400 fully staffed estates across 83-plus destinations, has released its winter portfolio for the season running December through April — a calendar that now divides into two versions of the same holiday. One is warm: the sun markets led by Turks & Caicos and Los Cabos, ranked second and sixth on the company's 2026 Billionaire Villa Index. The other is alpine: the catered chalets of Courchevel, Val d'Isère, Méribel, Verbier and Zermatt. Both run on the same operating standard — private chef, household team, 24/7 concierge — and, increasingly, on the same clock.
The timing of the announcement is not ceremonial. Traffic to the company's chalet pages has risen roughly fivefold month over month, according to the search data it tracks internally — the clearest signal yet that the winter decision, which once belonged to October, now begins in September.
The sun half: two top-ten markets
The warm side of the season is anchored by the two highest-ranked winter destinations on the company's index. Turks & Caicos, second overall, carries a collection of more than 160 handpicked villas across Grace Bay, Leeward, Turtle Tail and Long Bay, along with its private-island inventory. Winter is the market's defining season — the weeks when the Caribbean's most reliable weather meets its most international crowd.
Los Cabos, sixth on the index, is winter's newest argument at the top of the market. High season runs December through April, with dry weather, daytime temperatures between 75 and 82°F, and the grey-whale migration passing directly offshore — a natural spectacle that belongs exclusively to the winter months. The company's collection spans five enclaves, from Palmilla and Pedregal to the Tourist Corridor, with fully staffed estates typically running $3,000 to $8,000 a night and holiday weeks booking nine to twelve months ahead.
The snow half: where winter books earliest
The alpine side of the portfolio operates on the market's longest lead times. Across the company's French Alps collection — led by Courchevel 1850 in Les Trois Vallées, alongside Val d'Isère and Méribel — the top catered chalets are re-booked by the same families season after season, and the company's published guidance for Christmas, New Year and February weeks is twelve to eighteen months' notice. The properties are built for the way an alpine fortnight is actually spent: spas, cinema rooms, wine caves, and resident teams that absorb the lift passes, the instructors and the equipment before any of it reaches the guest.
That structural earliness is what makes the September search surge legible. Chalet demand arriving now is not early by the mountain's standards; it is on time, and it is the sun markets that are converging toward the alpine calendar rather than the reverse.
One standard under both climates
Every property in the winter release, whichever climate it stands in, runs through the same sequence the company applies year-round: a 21-day pre-arrival briefing on the specific family being hosted, a chef assigned against that brief rather than a rota, provisioning planned weeks ahead against supply chains that tighten at peak, and a concierge layer above the household for everything beyond the property line.
"Winter is the season where our guests stop choosing a destination and start choosing a temperature. The family that takes Los Cabos in January and Courchevel in February is taking the same holiday twice — the same chef standard, the same household, the same mornings that run themselves. What changes is what is outside the window. Everything we open today is built on that idea."
— Sabrina Piccinin, Founder and CEO, Haute Retreats.
A season that now starts in September
The practical reading of the opening is contained in its own data points. The alpine calendar asks for a year or more; Los Cabos holiday weeks ask for nine to twelve months; and search demand has already turned. A winter that once got decided in the last quarter of the year is now being decided in the first month of fall — and the fully staffed layer of the portfolio, in both climates, is the part that closes first. The company's Christmas and New Year 2026–27 collection is open now for both sides of the season.
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. Stay Exclusive. Live Extraordinary.
Media Contact
Angelica Crudo, Haute Retreats, 1 3054321731, [email protected], HauteRetreats.com
SOURCE Haute Retreats
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