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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Cortona holiday rentals

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 5.308.492 ₫
5.882.595 ₫ total
includes taxes & fees
20 Nov - 21 Nov
CASA AMBRA
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.573.710 ₫
2.888.752 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Vicolo Della Scala Rooms - La Luna
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is 2.876.484 ₫
3.221.803 ₫ total
includes taxes & fees
20 Nov - 21 Nov
Vicolo Della Scala Rooms - Il Sole
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

5. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (5 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is 1.655.360 ₫
2.326.725 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Limehome Arezzo Duomo
A bedroom with a large bed, a chandelier, a mirror, and plants.

6. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
"The BiBi was perfect for my needs. Its location is excellent, and the room had all the needed amenities. Fabio was a gracious host, orienting me to Arezzo and recommending a wonderful trattoria close by. I highly recommend and hope to return!"
United States
Carol
The price is 2.359.330 ₫
2.768.277 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Bibi Boutique
Pool

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (44 reviews)
"It was wonderful!"
United States
Wade
The price is 1.911.110 ₫
2.275.235 ₫ total
includes taxes & fees
8 Nov - 9 Nov
iConic Wellness Resort
A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.

8. 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 3.436.681 ₫
3.895.691 ₫ total
includes taxes & fees
9 Nov - 10 Nov
San Michele al Borgo
A crowded restaurant with brick walls and multiple tables and chairs.

9. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is 3.889.100 ₫
4.393.627 ₫ total
includes taxes & fees
25 Nov - 26 Nov
La Locanda di San Francesco
A terrace with a table set for breakfast, overlooking a scenic landscape.

10. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is 4.405.833 ₫
4.962.034 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Delcorto Suites
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

11. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
Fontelunga Hotel & Villas
A modern hotel room with large windows, a bed, a desk, and a chair.

12. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (85 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is 1.952.732 ₫
2.321.432 ₫ total
includes taxes & fees
12 Nov - 13 Nov
B&B 52cento
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

13. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (140 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is 5.945.380 ₫
6.655.260 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Il Tosco
An interior courtyard with stone columns, arches, and a mosaic.

14. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 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 4.118.890 ₫
4.646.397 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Meublé Il Riccio
A view of a historic town with prominent buildings and a church tower.

15. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Pros: Nice staff. Good breakfast with a nice view. Cons: Old bed and can feel the metal springs in your back so poor sleep. Lots of beggars and vagrants at the entrance of building."
United States
Steven
The price is 2.321.557 ₫
2.727.140 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Cameracaffè Centro
A spa area with a stone-walled arch, a hot tub, and a small window.

16. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.838.997 ₫
3.238.239 ₫ total
includes taxes & fees
9 Nov - 10 Nov
DormiVeglia B&B
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

17. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is 1.675.087 ₫
1.929.103 ₫ total
includes taxes & fees
2 Dec - 3 Dec
Abbadia Sicille Relais
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

18. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (170 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is 3.530.187 ₫
4.056.220 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
A courtyard with a pool, stone benches, and a view of a hill.

19. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (328 reviews)
"Beautiful garden, beautiful view, easy parking and tasty restaurant."
Canada
Sandro
The price is 5.756.638 ₫
6.534.150 ₫ total
includes taxes & fees
20 Nov - 21 Nov
TH Perugia - Castello di Monterone
Terrace/patio

20. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is 3.086.306 ₫
3.510.554 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Casale dell'Assiolo
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
"The highlight was the experience at the bar with the entertaining bartenders! Great breakfast and service!"
Stephanie 4-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa

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 171 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.