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 3,384 holiday lettings around Cortona. From 1,158 villas to 675 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.

Can I rent a rural property in Cortona?

There's nothing like the allure of a rural escape. Think relaxed strolls in nature, cosy local pubs and the melody of crickets at night. Yes please! HomeAway has 1,123 rural holiday properties in this destination. Searching for a different holiday vibe? See if any of our other properties catch your eye. Our options here include:

  • 589 village holiday accommodation options.
  • 185 mountainside holiday accommodation options.
  • 159 lakeside holiday accommodation options.

Can I rent a villa in Cortona?

Whether you're planning a family reunion, a rendezvous with friends or a big celebration, there's more than enough room for everyone when you choose a private villa. Just be sure to call dibs on the biggest bedroom! In this destination, you'll find 1,275 rentals to select from. Rates start from £26 per night. If that doesn't agree with your squad's taste, we have a range of other self-catering accommodation options to select from, such as:

  • Apartment: 1,204 self-catering accommodation options. Prices start from £26 per night.
  • House: 809 self-catering accommodation options. Prices start from £20 per night.
  • Farmhouse: 314 self-catering accommodation options. Prices start from £43 per night.

Can I stay in Cortona in a large group?

There's nothing quite like reuniting with old work colleagues or spending a week or so with your family in a wonderful new location. And what's best, HomeAway has options big enough for the whole crew. Why not check out the 248 apartment holiday rentals available here? They're the top option for big groups of travellers. Properties for rent in the area that can house large groups include:

  • Searching for places that can sleep 6 holiday makers? We have 625 that will be suitable. Prices start from £35 per night.
  • After a place for 8 people? We have 349 that will work well. The starting price is £58 a night.
  • Arranging a trip away with 5 guests? We offer 312 rental properties that will suit. Prices begin at just £37 per night.

You and all your besties will be more than satisfied when you organise your Cortona holiday through us!

Where are the cheapest holiday rentals in Cortona?

Show the door to sterile, drab chain-hotel rooms! Savour the flexibility of staying like a local in a budget-friendly holiday rental instead. Get a load of the diverse options available to book on HomeAway. When it comes to seeking out a great deal, the first place you look ought to be Ponte d'Oddi. Here, HomeAway has 37 holiday rentals at an average price of £58 per night. Another 9 HomeAway holiday rentals are available in or around Contrada Fontivegge. With an average price of £66 a night, you're sure to grab a deal worth bragging about.

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