Where MilanoStyle Readers Are Staying This Winter: Hotel Booking Trends Dataset

Here’s a vision of seasonal data on hotel booking trends that we think can be useful for both travelers and hospitality providers. Based on stays with check-in dates from November 2025 through March 2026 — a snapshot from real bookings made through MilanoStyle.com. These are the hotel booking trends showing how travelers choose their destinations.

MilanoStyle readers don’t “do winter” in one way. Yes, Milan is still the anchor—fashion-week energy, museum afternoons, aperitivo nights—but the booking trail also jumps quickly to airport-efficient stopovers, Alpine addresses, and a handful of surprisingly far-flung warm-weather resets. In other words: winter, styled.

What’s hot right now, hotel booking trends

• Milan leads the winter pack: it’s the most-booked destination in this data set (roughly 1 in 4 stays).
• Short stays are the default: the median stay is 1 night, suggesting quick city breaks, event-led overnights, and “in-and-out” travel weeks.
• Booking behavior is split: readers booked almost evenly on desktop vs. phone, which tracks with both spontaneous weekends and planned itineraries.
• Timing: winter stays were often booked close-in (median lead time ~11 days)—but spring/summer trips are being booked months ahead.
• The wildcard: among the quick one-nighters, there’s also the occasional long-stay escape that looks like a true “leave winter behind” moment.
• The current hotel booking trends suggest that spontaneity is key for many travelers.

Reader favorites

A snapshot of real bookings (November 2025–March 2026 stays).

Italy

TiAmo San Siro Apartment (Milan)

A practical, neighborhood-style base—especially smart when the reason you’re in town is event-led (matches, concerts, big weekends), and you’d rather feel local than lobby-bound.
Why to bookmark it: it’s famously close to San Siro—and even better, right by the M5 “San Siro Stadio” stop for clean, easy connections back into the city. Perfect this season for the Olympic games and opening ceremony event.

Ibis Milano Centro (Milan)

Readers still love a no-fuss, well-connected option in winter: warm room, easy transport, early trains, late dinners—Milan that works.
Detail to bookmark: there’s an on-site restaurant + bar (aperitivo-friendly) and a gym—handy when your days are built around meetings, museums, or winter walking.

Hotel Villa La Bollina (Serravalle Scrivia)

This is the “style-meets-strategy” booking: a stay that pairs beautifully with outlet shopping and a slower countryside rhythm—perfect for a winter reset that’s still close to Milan.
Why to bookmark it: it’s set inside the park of the Serravalle Golf Club and has a fine-dining restaurant, TRACCE, for a stay that feels deliberately “occasion-worthy.” Its also minutes away from the Serravalle Designer Outlet that has over 230 fashion brands and boutiques with everything from sportswear to designer jeans to luxury fashion like Gucci, Prada, Valentino and more.

Other locations in Italy

Cernobbio, Lake Como

Lake Como doesn’t disappear in winter—it simply becomes more intimate. A Cernobbio stay signals quiet lake walks, warm interiors, and the kind of calm you can’t schedule.
Why to bookmark it: Cernobbio is home to icons like Villa d’Este, where the lakefront setting is practically a ritual—and the spa is legendary.

Florence

Florence in late winter/early spring is a connoisseur move: fewer crowds, sharper museum days, and evenings that still feel like an occasion.
Why to bookmark it: Florence needs no introduction, but remember, the Uffizi isn’t just “a museum day”—it’s centrally placed near Piazza della Signoria, and even has a panoramic terrace cafeteria for a perfectly timed break. Florence is a great starting point for exploring Tuscany or before heading further south towards Rome or Naples.

Casorate Sempione, Malpensa area

A classic “smart stop”: when timing matters—early flights, late arrivals—readers book for ease, not drama.
Why to bookmark it: This area is well-positioned for Malpensa (quick rail links), and if you have a spare hour, Volandia (the aviation museum) is right by the airport—an unexpectedly good add-on.

Beyond Italy

Samedan: Romantik Hotel Muottas Muragl (Switzerland)

This one reads like pure Alpine intention: views, crisp air, and the sort of winter atmosphere that makes you forget your email exists. Rise to new heights for a new perspective and fresh air.

Geneva: Nash Airport Hotel (Switzerland)

A winter favorite for travelers who value efficiency with comfort—the kind of booking that says “I’m here for a purpose” (and I’ll still sleep well).

Faro (Portugal)

A winter sun signal. Even without the full itinerary, Faro reads like light, sea air, and an early taste of spring. The Algarve in spring is warm enough for a vacation yet still quiet enough to enjoy without the holiday crowds.

Paracas: Bamboo Paracas Hotel (Peru)

The standout long-stay booking in this data set. When readers go long in winter, they go decisively—this looks like a full reset, not a weekend away.

Eastern Europe Getaways

Keep an eye on Eastern Europe getaways this season. Our readers are quietly booking cities that deliver atmosphere without the crowds. Cracowdays (Krakow, Poland) signals a winter city break done right: walkable streets, culture on tap, and café pauses that feel like part of the itinerary, not a break from it.

And then there are the more “insider” routes such as Safir Hotel Casino (Sežana, Slovenia) and Hotel Studio (Veliko Tŭrnovo, Bulgaria)—both suggest travelers who enjoy going slightly off-map, whether it’s a border-hopping drive or a heritage-rich town that still feels refreshingly residential.

We’re already seeing Spring & Summer Trends

MilanoStyle readers are already planning ahead (May–July stays in from the same report):

The early signals point to a classic mix of Italian icons with big-ticket long-haul trips: Rome, Venice, Florence, Pisa, Ravenna, and even Àrbatax (Sardinia). US destinations such as San Diego and Las Vegas are also leadign the way. What’s most telling isn’t just where, but when: these trips were booked 4–8 months in advance, a very different rhythm than winter’s quick stays and most likely part of a curated vacation plan.

Check back soon: the spring/summer “where readers are staying next” list is already quietly forming.

For more on hotel booking trends, check out our latest articles and insights:

• Where MilanoStyle Readers Are Booking This Autumn: Style, Serenity & City Breaks

• Where MilanoStyle Readers Stayed This Summer: The Most Booked Hotels in Italy

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MilanoStyle.com: Behind the Scenes

Data for trend geeks

• 15 winter stays in this snapshot (check-ins Nov–Mar)
• Median stay length: 1 night
• Devices: nearly split between desktop and phone
• Providers: most bookings here ran through Booking.com, with Expedia also active

Micro-trends we’re seeing

• “Anchor + add-on” travel: Milan as the core, with a second destination layered in (lake, Alps, or a quick European hop).
• Winter practicality, spring romance: short lead times in winter, longer lead times for warm months.
• Readers are comfortable going niche: several bookings are for places that aren’t mainstream “top 10” lists.

Methodology

This article is based on our B2B affiliate booking data exported from MilanoStyle.com, filtered to ACCOMMODATION stays with check-in dates between November 2025 and March 2026 (with an added look at May–July 2026 for the teaser). It’s a snapshot—useful for spotting patterns, not declaring absolutes.

The Data

This data was compiled from our B2B affiliate platform Stay22, which aggregates various accommodation options such as Booking, Vrbo, Expedia, Agoda, GetYourGuide and Hotels.com and provides users with tailored recommendations based on their preferences and travel habits. If you manage a travel platform or blog, join Stay22 and get better booking conversions.
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