Villas in Lombardy in winter

Madesimo suits ski weeks close to Milan, Bormio suits skiers after thermal baths and an old town, and Livigno suits high-altitude slopes. Despite the name, this covers the Lombardy Alps all year: ski flats and chalets in the Valchiavenna, Valtellina and Val Camonica, with walking and cycling in summer. Expect long transfers.

Where

Villas: 93
From, per week: £307
Cheapest month: October
Nearest airports: Milan Malpensa, Milan Linate and Bergamo for most resorts, around two hours to Madesimo and three or more to Bormio and Livigno. Zurich is an option for Livigno via Switzerland. Flights from London to Milan take around one and three-quarter hours.

Where to stay in Lombardy in winter

Madesimo and Campodolcino (Valle Spluga)

Madesimo and Campodolcino hold nearly half of our homes here. Together with Motta they make up the Valchiavenna ski area, and a cable car runs from Campodolcino up to Motta to join the slopes. In summer the Spluga pass opens to Switzerland and the valley is good walking country. Chiavenna, half an hour below, has stone grotto restaurants built into the rocks. Milan's airports are around two to two and a half hours away.

Best for: Skiers who want the shortest transfer from Milan

Not for you if: You want a big international resort: this is a mostly Italian, weekend-busy ski area.

Bormio and Oga (upper Valtellina)

Bormio has as many of our homes as Madesimo. It is a real town with a medieval centre, three thermal spas and the Stelvio piste, which hosted the men's alpine races at the 2026 Winter Olympics. Oga, on the hillside above, is close to the San Colombano ski area and a First World War fort. In summer the Stelvio and Gavia passes draw cyclists, and the Stelvio National Park starts on the edge of town.

Best for: Skiing followed by an evening in the thermal pools

Not for you if: You want an easy drive in: Bormio is around three hours or more from Milan.

Livigno

Livigno sits at around 1,800 metres in a long high valley near the Swiss border, with two ski areas, Carosello 3000 and Mottolino, on either side. It hosted the snowboard and freestyle events at the 2026 Olympics and has duty-free status, so fuel and shopping are cheaper. In summer it is a mountain biking centre. From Bormio the road over the Foscagno pass takes around an hour. Choice is small: only a handful of homes.

Best for: High-altitude skiing, snowboarding and duty-free shopping

Not for you if: You want a quick journey: every road in crosses a high pass or a single-lane tunnel.

Aprica and the middle Valtellina (Aprica, Grosotto, Torre di Santa Maria)

Aprica is a mid-sized ski resort on the pass between the Valtellina and the Val Camonica. Grosotto is a valley village between Tirano, where the Bernina Express leaves for St Moritz, and Bormio. Torre di Santa Maria is in the Valmalenco, a side valley above Sondrio with its own small ski area. The terraced vineyards along the valley make Nebbiolo red wine, and the local dish is pizzoccheri, a buckwheat pasta.

Best for: Budget ski weeks and Valtellina wine and food

Not for you if: You want plenty of choice: we have only a few homes here.

Ponte di Legno and the Val Camonica (Ponte di Legno, Berzo Demo)

Ponte di Legno is linked by lift to the Passo del Tonale in Trentino, and together they run up to the Presena glacier, which helps keep the season long. Berzo Demo is lower down the Val Camonica, near Capo di Ponte, where thousands of prehistoric rock carvings make up Italy's first UNESCO World Heritage Site. Bergamo airport is around two hours away.

Best for: Skiing linked to the Tonale pass and a glacier

Not for you if: You want lots of homes to choose from: there are only two.

When to go to Lombardy in winter

The ski season usually runs from early December to around Easter, a little longer at high Livigno. Christmas, New Year and February weekends are busiest, when Milan's skiers arrive. January is quieter. Summer, from late June to mid-September, suits walking, road cycling and mountain biking, and the high passes such as the Stelvio and Spluga are only open in the warmer months. May, October and November are dead seasons: many lifts, hotels and restaurants close.