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

Cortona Vacation Rentals

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Check prices for these dates

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

Our top choices for Cortona vacation 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 ₩217,695
₩245,846 total
includes taxes & fees
Sep 23 - Sep 24
B&B Piccolo Hotel
Deluxe Apartment, City View | Soundproofing, iron/ironing board, WiFi (free)

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ₩456,791
₩507,255 total
includes taxes & fees
Oct 1 - Oct 2
CASA AMBRA
Apartment (1 Bedroom) | Front of property

3. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ₩159,124
₩181,418 total
includes taxes & fees
Sep 21 - Sep 22
Vicolo Della Scala Rooms - Il Sole
Apartment (1 Bedroom) | Front of property

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ₩142,375
₩162,993 total
includes taxes & fees
Sep 26 - Sep 27
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 ₩130,875
₩150,343 total
includes taxes & fees
Sep 21 - Sep 22
Residence al Lago
Interior

6. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (118 reviews)
"It was very well located ."
Canada
Marlenne
The price is ₩227,309
₩256,421 total
includes taxes & fees
Sep 23 - Sep 24
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 ₩133,413
₩156,325 total
includes taxes & fees
Oct 15 - Oct 16
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 ₩301,628
₩338,172 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩187,606
₩212,746 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩289,425
₩327,932 total
includes taxes & fees
Oct 6 - Oct 7
Hotel San Gregorio
Seasonal outdoor pool, sun 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 ₩289,738
₩329,878 total
includes taxes & fees
Sep 30 - Oct 1
TH Perugia - Castello di Monterone
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun 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 ₩120,077
₩141,656 total
includes taxes & fees
Oct 11 - Oct 12
iConic Wellness Resort
Suite Aria | Terrace/patio

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (43 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ₩261,628
₩294,171 total
includes taxes & fees
Sep 20 - Sep 21
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 ₩198,903
₩225,136 total
includes taxes & fees
Sep 29 - Sep 30
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 ₩191,444
₩215,373 total
includes taxes & fees
Oct 12 - Oct 13
Abbadia Sicille Relais
Panoramic Cottage, 1 Bedroom | 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 ₩154,658
₩209,844 total
includes taxes & fees
Oct 4 - Oct 5
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 ₩447,293
₩498,403 total
includes taxes & fees
Sep 24 - Sep 25
Il Tosco
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | 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 ₩157,050
₩179,136 total
includes taxes & fees
Oct 4 - Oct 5
DormiVeglia B&B
Exterior detail

19. Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is ₩108,586
₩122,635 total
includes taxes & fees
Sep 20 - Sep 21
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 ₩118,374
₩136,593 total
includes taxes & fees
Oct 13 - Oct 14
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"There was nothing to be improved because everything was perfection!!"
Michelle 3-night trip
Posted 17 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

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

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

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a 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 theater during your trip.

How many vacation rentals are there in Cortona?

With 167 Expedia vacation rentals, you're sure 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 vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.