Destination guide

Vistas of Italy in Cortona

The red-tiled roofs and terracotta towers of Cortona keep watch over the Tuscan plains just as they have done for centuries. Calling it picturesque doesn't nearly do it justice. The cobblestone streets drape over the hillside, making way for the crenellated keeps of the medieval piazzas, now host to bustling cafes and trattorias and Saturday markets. You'll be wowed by the long history, featuring Etruscans and Romans. You'll be seduced by the fine Arezzo wines. You'll be bewitched by all sorts of Cortona holiday rentals, from rustic villas on the surrounding peaks to romantic boltholes in the centre.

Things to do

Wines and Etruscan tales in Cortona

It's impossible to come to stay in a Cortona holiday rental and ignore the town's long, long history. Local guides will be able to reveal the remnants of Etruscan and Hellenistic tombs in the dispersed Archaeological Park of Cortona outside the city walls. Back inside, the famous Diocesan Museum is a place to gawp at great triptychs and artworks of the Italian Renaissance, or encounter the carved tombs of Roman nobles. Then the wine calls. The Molesini and Baracchi wineries are just a stone's throw from the centre – get ready to taste.


Cortona's culinary flare

Views aside, Cortona is an authentic slice of Tuscan traditionalism. The streets that fly off from little Piazza Repubblica are awash with antique delicatessens, all bursting with buffalo mozzarella, fresh mountain herbs, fruity olive oils, hand-roasted coffee beans and peppered meat cuts. Cooking lessons with a local are a good way to dip your toe in the region's cuisine – forget pizzas, this is all about hearty stews and pappa al pomodoro. Alternatively, wait for the weekend market, a whirlwind of porchetta sandwiches and stacked tomatoes. No wonder Cortona holiday rentals with kitchens are so sought after.


Cortona's many seasonal faces

There's no hard and fast rule about when's the best time to visit Cortona. Seeking a family villa with a pool on the Italian hills? Summer's the best choice. There are dry, warm days aplenty between June and August. Prefer to explore the town's long history or culinary character? A spring trip – in September or October – could help save you a heap of euros to spend on truffle pastas and Tuscan T-bone steaks. More unusual are winter breaks between December and March, which could mean catching Cortona and the Apennines blanketed in snow.

Natural features

Clutching the Tuscan hills

Cortona clings to one of the last foothills of the Italian Apennines before the rolling plains of central Italy and the undulating landscapes of Tuscany take over. That means the eastern side of town is given over to mountains that forever rise and rise, clad in galleries of chestnut forests and pines. The western side, meanwhile, drops down to the Arezzo valley. You'll find endless farms and green fields and vineyards there, not to mention the vast Lake Trasimeno, with its islets and wooded shores.

How to get there

Transport to and around Cortona

The nearest airport is in Perugia (PEG-Sant Egidio), located 28.9 mi (46.6 km) from the city centre.

If you prefer train travel, make your way to Camucia-Cortona Station or Terontola-Cortona Station and explore the city from there.

How many holiday rentals are available around Cortona?

Our 2020 accommodation listings offer a large selection of 3,371 holiday lettings around Cortona. From 1,153 villas to 677 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Cortona? offers a large selection of holiday accommodations near great places in Cortona. From travellers, the most popular points of interest to stay near are:

  • Camucia-Cortona Station: 4,171 holiday lettings
  • Palazzo Comunale: 4,107 holiday lettings
  • Terontola-Cortona Station: 4,115 holiday lettings
  • Farneta Abbey: 4,351 holiday lettings
  • Santa Maria delle Grazie: 4,075 holiday lettings

But there are many other points of interest around Cortona listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Villas in Cortona?

Yes, of course. offers 1,153 Villas in Cortona. Our other popular types of Cortona holiday rentals include:

  • Houses: 677 self catering accommodations
  • Farmhouses: 258 self catering accommodations
  • Flats: 990 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Cottages and more.

Can I find a holiday accommodation with pool in Cortona?

Yes, you can select your preferred holiday accommodation with pool among our 2,744 holiday homes with pool available in Cortona. Please use our search bar to access the selection of holiday rentals available.

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