Cortona, Arezzo, Italy

Cortona, Arezzo, Italy

We found 3,864 vacation rentals — enter your dates for availability


Find the best place to stay — Cortona

Where to stay around Cortona, IT?

Our 2018 property listings offer a large selection of 3,864 vacation rentals near Cortona. From 1,416 apartments to 1,316 villas, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Cortona for a holiday or a weekend are on HomeAway.

Medieval magic in Cortona

Tucked in the southern region of Tuscany, Cortona dazzles with its ancient stone walls, medieval architecture and spectacular views from its prime hilltop location. Cortona vacation rentals provide an excellent base for exploring exquisitely preserved religious sites, tasting the spectacular wines of the region or taking a class on traditional Tuscan cuisine. There are museums to inspire, with the fascinating history of the many cultures that have thrived in Cortona, and, at the end of the day, you can watch the sunset over surrounding hills, as you sip wine and watch people from a comfortable seat in a piazza.

History and art in Cortona

Lovers of history will find myriad delights in the medieval city of Cortona. The old walls of Cortona hold a wealth of stories, with a history incorporating the ancient Etruscans, the Romans, the powerful Medici family and Francis of Assisi, Cortona vacation rentals are within walking distance of many of Cortona's most important sites. Art lovers will find much to inspire in museums and galleries, while shoppers can wander the narrow streets to find treasures of local wines, produce and crafts. For a break from the heat, take a refreshing dip in the waters of nearby Lake Trasimeno.

A hilltop fortress in Cortona

Housed in a gorgeous 13th-century palazzo, the Museo dell'Accademia Etrusca e della Città di Cortona is a riveting museum, filled with Roman and Etruscan treasures unearthed from the surrounding area. For staggeringly beautiful views of Tuscany and Umbria, the Medici fortress, Fortezza del Girifalco, cannot be beaten. Once you've soaked up the view, you can stay for a falconry show or dinner concert. The Eremo Francescano Le Celle, a Franciscan hermitage, is a short drive from Cortona vacation rentals. Nestled in the woods across an old stone bridge, it's a place of stillness broken only by the toll of bells.

Springtime beauty in Cortona

If you want to explore the medieval beauties of Cortona without sweltering or shivering, spring is the best time of year to visit. April and May are ideal, with warm, sunny afternoons for wandering the cobbled streets, and cool mornings to explore the nearby hills, carpeted in wild flowers. Summer is a beautiful time to visit Cortona, but the temperatures soar, so be sure to wear a hat and keep hydrated. Fall is great for sampling the bounty of Cortona, and winter, although chilly, is still a beautiful time to stay in Cortona and take daytrips for downhill skiing.

Hillside wonders and wildlife in Cortona

Cortona is perched on a hilltop, with stunning views of a countryside marked by rolling hills and verdant farmland. Around 2 hours east of the Adriatic Sea and 2 hours west of the Tyrrhenian Sea, Cortona is ideally situated for those who want to experience medieval architecture, rural idylls and seaside excursions. Cortona is known more for food and wine than wildlife, but those who venture out of the city and into the countryside will have the opportunity to see wild animals. Trekking over the hills affords the best chance to spot wild boar, wolves, porcupines, badgers and red foxes.