Just 5 miles from Montalcino, Castello Di Velona is a 10th-century-castle-turned-luxe-resort in one of Italy's top wine regions. This former fortress sits atop a hill overlooking the Val d’Orcia’s breathtaking olive groves, cypress trees and sweeping vineyards renowned for producing Brunello wine. Unwind in the resort's thermal water pools and explore the spectacular flavors and sights of Tuscany with this offer that includes accommodations in a suite with views of Castle Brunello, a wine tasting (Brunello, of course), a lunch for two and more.

Head to these three iconic Italian destinations this winter for under $800.

Nestled deep in the vineyards of Valpolicella is Byblos Art Hotel Villa Amistà—a stunning 16th-century villa that features an eclectic blend of Venetian elegance with colorful modern and contemporary art from world-class artists such as Damien Hirst and Anish Kapoor. Uniquely designed rooms, an on-site Michelin-starred restaurant, a luxe spa with a Turkish bath and a 15th-century wine cellar complete the 5-star experience. Travelzoo members can save up to 50% on 3-night stays with this offer that includes daily breakfast, a three-course dinner for two, a small bottle of red wine and daily access to the spa.

This historic farm-turned-villa is in the heart of Tuscany's famously picturesque countryside near Siena, Perugia, Florence and the UNESCO-listed Val d'Orcia. Save up to 50% with this offer that covers 5 nights in a spacious villa, daily breakfast, a private truffle hunt, a wine tasting, a truffle dinner and more.

We sourced some of our members' favorite deals across four continents, which include guided tours, excursions, flights, transfers and more.