A hillside town with historic buildings, a church, and vineyards.

Cortona Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Cortona holiday rentals

Lobby

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is HK$1,230
HK$1,389 total
includes taxes & fees
23 Sept - 24 Sept
B&B Piccolo Hotel
Soundproofing, iron/ironing board, free WiFi

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is HK$2,580
HK$2,865 total
includes taxes & fees
1 Oct - 2 Oct
CASA AMBRA
Front of property

3. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is HK$899
HK$1,025 total
includes taxes & fees
21 Sept - 22 Sept
Vicolo Della Scala Rooms - Il Sole
Front of property

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is HK$804
HK$921 total
includes taxes & fees
26 Sept - 27 Sept
Vicolo Della Scala Rooms - La Luna
Front of property

5. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 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 HK$739
HK$849 total
includes taxes & fees
21 Sept - 22 Sept
Residence al Lago
Interior

6. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is HK$1,284
HK$1,448 total
includes taxes & fees
23 Sept - 24 Sept
Meublé Il Riccio
Porch

7. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (192 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
The price is HK$745
HK$874 total
includes taxes & fees
15 Oct - 16 Oct
Cameracaffè Centro
Food court

8. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (147 reviews)
"Incredible views from our room"
United Kingdom
Isabelle
The price is HK$1,704
HK$1,910 total
includes taxes & fees
27 Sept - 28 Sept
La Locanda di San Francesco
Exterior

9. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is HK$1,060
HK$1,202 total
includes taxes & fees
27 Sept - 28 Sept
Bed & Breakfast Vicolo dell'Oste
Food and drink

10. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (157 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is HK$1,620
HK$1,837 total
includes taxes & fees
6 Oct - 7 Oct
Hotel San Gregorio
Seasonal outdoor pool, pool loungers

11. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (320 reviews)
"Breakfast was not impressive and very warm room with mosquitoes"
Canada
Baudouin
The price is HK$1,637
HK$1,863 total
includes taxes & fees
30 Sept - 1 Oct
TH Perugia - Castello di Monterone
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

12. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is HK$678
HK$800 total
includes taxes & fees
11 Oct - 12 Oct
iConic Wellness Resort
Terrace/patio

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (44 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is HK$1,526
HK$1,715 total
includes taxes & fees
6 Oct - 7 Oct
Delcorto Suites
Exterior

14. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is HK$1,130
HK$1,279 total
includes taxes & fees
21 Sept - 22 Sept
San Michele al Borgo
Front of property – evening/night

15. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (182 reviews)
"Great Historical location."
Canada
Robert
The price is HK$1,081
HK$1,216 total
includes taxes & fees
12 Oct - 13 Oct
Abbadia Sicille Relais
Exterior

16. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (66 reviews)
"A fantastic stay in such a beautiful part of Tuscany. Hosts were friendly and went out of their way to help. Breakfast was lovely and the room was clean and comfortable. Would highly recommend!"
United Kingdom
Christopher
The price is HK$874
HK$1,185 total
includes taxes & fees
4 Oct - 5 Oct
Affitacamere Maria Gabriella
Property entrance

17. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (131 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is HK$2,526
HK$2,815 total
includes taxes & fees
24 Sept - 25 Sept
Il Tosco
Private spa tub

18. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is HK$887
HK$1,012 total
includes taxes & fees
4 Oct - 5 Oct
DormiVeglia B&B
Exterior detail

19. Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is HK$613
HK$693 total
includes taxes & fees
21 Sept - 22 Sept
Il Rifugio del Borgo
Property entrance

20. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (109 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is HK$669
HK$772 total
includes taxes & fees
14 Oct - 15 Oct
Residenza Fabroni
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.
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Top Cortona Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Beren 2-night trip
Posted 1 hour ago
Villa di Piazzano - Small Luxury Hotel of the World

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
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  • 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.

What are some of the best holiday rentals that Cortona has to offer?

Beautiful tuscan villa with pool, ideal for groups: This highly rated holiday home rental in Cortona is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. Some other top choices in Cortona are Casa Fontelunga, Tuscan holiday villa with private pool and Casa Bacco - private house with a remarkable garden in the centre of Cortona.

How many holiday rentals are there in Cortona?

With 167 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 Villa Bramasole 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.