Search Holiday Rentals in Cortona

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Cortona holiday rentals

Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ฿4,105
฿4,666 total
includes taxes & fees
20 Apr - 21 Apr
B&B Piccolo Hotel
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ฿3,353
฿3,838 total
includes taxes & fees
23 Apr - 24 Apr
Vicolo Della Scala Rooms - La Luna
Deluxe Apartment, City View

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ฿5,840
฿6,536 total
includes taxes & fees
29 Apr - 30 Apr
CASA AMBRA
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ฿3,763
฿4,290 total
includes taxes & fees
20 Apr - 21 Apr
Vicolo Della Scala Rooms - Il Sole
Exterior detail

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is ฿3,704
฿4,149 total
includes taxes & fees
19 Apr - 20 Apr
Il Rifugio del Borgo
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ฿2,840
฿3,350 total
includes taxes & fees
4 May - 5 May
iConic Wellness Resort
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is ฿5,353
฿6,039 total
includes taxes & fees
19 Apr - 20 Apr
Meublé Il Riccio
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (172 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿4,876
฿5,477 total
includes taxes & fees
26 Apr - 27 Apr
Abbadia Sicille Relais
Outdoor pool, pool loungers

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (307 reviews)
"Beautiful hotel in restored castle. Staff were kind and welcoming. "
United Kingdom
Stuart
The price is ฿6,173
฿7,054 total
includes taxes & fees
23 Apr - 24 Apr
Castello di Monterone
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is ฿3,301
฿3,782 total
includes taxes & fees
19 Apr - 20 Apr
Bed & Breakfast Vicolo dell'Oste
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (53 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
The price is ฿3,812
฿5,132 total
includes taxes & fees
20 Apr - 21 Apr
Affitacamere Maria Gabriella
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (134 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is ฿5,212
฿5,885 total
includes taxes & fees
28 Apr - 29 Apr
La Locanda di San Francesco
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is ฿6,211
฿6,983 total
includes taxes & fees
12 May - 13 May
Casanova - Panoramic Rooms and Suites
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (181 reviews)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is ฿3,483
฿4,057 total
includes taxes & fees
19 May - 20 May
Cameracaffè Centro
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
The price is ฿7,583
฿8,567 total
includes taxes & fees
4 May - 5 May
Hotel San Gregorio
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (98 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ฿2,654
฿3,071 total
includes taxes & fees
20 Apr - 21 Apr
Residenza Fabroni
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ฿2,078
฿2,286 total
includes taxes & fees
21 Apr - 22 Apr
L'Antica Sosta
Front of property

Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (37 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is ฿3,017
฿3,469 total
includes taxes & fees
19 May - 20 May
Residence al Lago
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is ฿5,814
฿6,546 total
includes taxes & fees
19 Apr - 20 Apr
Delcorto Suites
Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (10 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is ฿4,007
฿4,483 total
includes taxes & fees
19 Apr - 20 Apr
La Piccola Locanda
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"It was the nicest and most unique hotel stay and experience we’ve ever had! From the front desk staff to the restaurant and bar staff was beyond our expectations! The attention to detail from the cleaning staff and the spa was unbelievable! Hard to mention everyone. Every employees attention to detail makes this experience! The hotel is beyond stunning ! This hotel sets a high bar and absolutely met it with flying colours! "
James 3-night trip
Posted 8 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday apartments in Cortona using one of the methods below:

  • View our selection of featured holiday rentals in Cortona
  • Use the map to find apartments and other holiday homes in the Cortona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cortona while they last

Look no further and take a look at our great range of rental properties in Cortona!

Frequently asked questions

Can I find holiday rentals in Cortona?

Yes, there are holiday rentals close to the most popular sights in Cortona, or you can select a more secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theatre during your trip.

How many holiday rentals are there in Cortona?

With 145 Expedia holiday rentals, you're guaranteed to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Cultural attractions include Museum of the Etruscan Academy and Signorelli Theatre, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Giuseppe Garibaldi Memorial are other places worth a visit.

What’s a holiday rental in Cortona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cortona. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.