Vacation Rentals in Cortona

Vacation Rentals in Cortona

Start comparing over 166 rentals in Cortona and book at the best price!

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Highlights Cortona

  • Visit to the Cathedral of the Assumption of the Virgin Mary
  • Visit of the church Madonna del Calcinaio
  • Museum tour in Piazza della Repubblica

Best Vacation Rentals in Cortona

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 7 Guests in Cortona, Arezzo Province
Vacation Rental for 7 Guests in Cortona, Arezzo Province, Picture 1
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Cortona, Arezzo Province
Vacation Rental • 1507 ft² • 3 Bedrooms
9.8
(99 reviews)
The farmhouse "La casa del nonno Bingheri" is an old and typical farmhouse of the Tuscan countryside. It is a wisely restored rustic house in which three lovely apartments have been obtained and from which, you can enjoy a splendid view of the hill cone of Cortona. The careful restoration work has made it possible to preserve and enhance the pre-existing structure, enriching it with modern comforts. All our apartments are spacious, bright, have a terrace and independent entrance. Outside the apartments have a private space furnished with table, chairs, sofas. There are 3 bathrooms with show...
from $212 / night
Vacation Rental for 3 Guests in Cortona, Arezzo Province
Vacation Rental for 3 Guests in Cortona, Arezzo Province, Picture 1
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Cortona, Arezzo Province
Vacation Rental • 538 ft² • 1 Bedroom
9.4
(17 reviews)
Traveling along the road between Tuscany and Umbria, you’ll reach Pierle, a medieval village perched on the hills between Cortona and Lake Trasimeno, with its castle overlooking the green valley below. Here, surrounded by olive trees and chestnut and oak woods, lies our agriturismo. The La Loggetta apartment is on the upper floor, accessible via stone stairs leading to a small terrace. Inside, you’ll find a bright living room with a sofa, dining table, TV, stereo, and an antique stone fireplace. The sleeping area is separated by a door opening onto a landing, leading to a spacious bedroom w...
from $113 / night
Vacation Rental for 10 Guests in Cortona, Arezzo Province
Vacation Rental for 10 Guests in Cortona, Arezzo Province, Picture 1
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Vacation Rental for 10 Guests in Cortona, Arezzo Province, Picture 4
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Cortona, Arezzo Province
Vacation Rental • 2045 ft² • 5 Bedrooms
9.5
(17 reviews)
Traveling along the road between Tuscany and Umbria, you’ll reach Pierle, a medieval village nestled in the hills between Cortona and Lake Trasimeno, with its castle overlooking the green valley below. Here, surrounded by olive groves and chestnut and oak woods, you’ll find the farmhouse. Agriturismo Pierle Cuiano La Loggia is on the second floor, accessed by stone steps leading to a spacious covered terrace with breathtaking views of Pierle Castle—perfect for dining, reading, or relaxing outdoors. The large, bright living room features a sofa, armchairs, TV, stereo, and an antique stone fi...
from $394 / night

Other holiday ideas and property types in Cortona that might be interesting

Popular Destinations in Cortona

    Prices and availability

    Current Vacation rental prices Cortona

    $297for 10 Oct - 17 Oct
    $326 annual average
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    Average price per week

    Current vacation rental availability Cortona

    38%for 10 Oct - 17 Oct
    48% annual average
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    Percentage of available rentals

    Vacation rentals in Cortona

    Typical holiday accommodations in Tuscan style

    In Cortona, Italy, you will find typical holiday accommodations for singles, couples and families. Choose a practically equipped holiday apartment in the medieval old town for two people or opt for a modern apartment for up to four people in the interior. A luxurious vacation rental in Tuscan style is recommended for a relaxing holiday with the whole family.

    Holidays in Cortona

    Location and orientation

    Etruscan city in Italian Tuscany

    The city of Cortona lies as one of the oldest settlements within the province of Arezzo in Italy. Belonging to the region of Tuscany, the Etruscan city of Cortona borders the province of Siena to the south and the Umbria region to the east. With its hillside location on a mountain range that separates the Chiana Valley from the Tiber Valley, the Chiana Canal, which gives the town its name, flows through the extensive urban area, which consists of a total of 23 other districts.

    Things to know

    With the first medieval festival "Giostra dell'Archidado", held in 1397, a traditional historical event has taken place in Cortona every year since 1994. Five districts of the city still compete against each other in the crossbow shooting discipline in Piazza Signorelli.
    According to legend, founded by the Etruscan people, the Etruscan name Cortonas is "Curtun".

    Top 3 travel tips

    1st visit to the Cathedral of the Assumption of the Virgin Mary

    Cortona offers you a cultural and historical highlight in the form of a visit to the historic Cathedral of the Assumption of the Virgin Mary. Built near your vacation rental on the massive foundations of an ancient temple, the parish church was first documented in the 11th century. The architecture of the impressive cathedral includes a Romanesque core, which was transformed into an elegant Renaissance building in the middle of the 15th century and later adapted to the Baroque style.

    2nd visit to the Madonna del Calcinaio

    The church of Madonna del Calcinaio is considered one of the most important works of art in Cortona. Visit the church built by the painter and sculptor Francesco di Giorgio Martini in the years 1484 to 1515 which was built after the miraculous model of a picture of the Virgin Mary. This painting today adorns the shrine of the host above the high altar of the church. Also visit the unusually high vaults inside and admire the impressive Renaissance architecture of the Madonna del Calcinaio.

    3rd museum tour in Piazza della Repubblica

    Close to your holiday home, the Piazza della Repubblica is the ideal starting point for museum tours through the city centre as an urban centre. In addition to the well-preserved medieval townscape and the panoramic view over the Chiana Valley, the two museums "Museo dell'Accademia Etrusca" and the Diocesan Museum are worth seeing attractions. The former houses a rare Etruscan collection, while the latter houses exhibitions of important works by renowned Renaissance artists.

    FAQs: Vacation Rentals in Cortona

    How much does it cost to book a vacation rental in Cortona?

    Last year, rentals in Cortona had an annual average price of around $260 per night.

    What time of year offers, on average, the best vacation rental prices in Cortona?

    If you would like to save the maximum during your visit to Cortona, pack your bags and travel there in November ($229 per night on average), March ($232), or April ($234), to find the lowest prices for the whole year.

    When are vacation rentals more expensive in Cortona?

    Last year, the month that showed the highest annual average prices in Cortona was August, with an average price of $302 per night. This was followed by July, with an average of $295, and then January, with $279.

    Is Cortona a good location for a last-minute getaway?

    Here, last-minute travelers are welcome, because the average availability in Cortona is 59%, which is above average for Italy, based off last year.

    What time of the year can I find more available vacation rentals?

    May, April and June are, in order of highest to lowest, the months offering the largest number of accommodations free, with an average availability of 81%, 80%, and 76%. During this period, you will have a wide section to choose from.

    When are fewer rentals available in Cortona?

    The month with the highest average booked rental figures is August (only 23% of properties were available on average last year). Followed by December (48%), and then January (51%).

    How many vacation rentals does Holidu have in Cortona?

    We have grouped together the offers from 28 different partners in Cortona, so we can provide you with around 530 properties. You're going to have a hard time choosing!