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

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 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 4.118.481 ₫
4.651.041 ₫ total
includes taxes & fees
23 Sept - 24 Sept
B&B Piccolo Hotel
Deluxe Apartment, City View

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 3.703.571 ₫
4.164.462 ₫ total
includes taxes & fees
17 Sept - 18 Sept
CASA AMBRA
Apartment (1 Bedroom) | Front of property

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.693.528 ₫
3.083.593 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Vicolo Della Scala Rooms - La Luna
Apartment (1 Bedroom) | Front of property

4. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is 3.010.398 ₫
3.432.150 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Vicolo Della Scala Rooms - Il Sole
Exterior

5. 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 3.785.974 ₫
4.285.284 ₫ total
includes taxes & fees
13 Sept - 14 Sept
San Michele al Borgo
Courtyard

6. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is 8.536.224 ₫
9.510.730 ₫ total
includes taxes & fees
19 Sept - 20 Sept
Fontelunga Hotel & Villas
Pool

7. 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 2.271.683 ₫
2.679.920 ₫ total
includes taxes & fees
11 Oct - 12 Oct
iConic Wellness Resort
Outdoor dining

8. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (44 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is 6.515.716 ₫
7.288.000 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Castello di Gargonza
Food court

9. 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 6.035.610 ₫
6.759.883 ₫ total
includes taxes & fees
8 Oct - 9 Oct
La Locanda di San Francesco
Junior Suite | Terrace/patio

10. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is 3.333.377 ₫
3.787.427 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Casale dell'Assiolo
Exterior

11. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.189.281 ₫
2.528.921 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Artisti del Cavallo Tourism
Interior

12. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (117 reviews)
"It was very well located ."
Canada
Marlenne
The price is 4.300.373 ₫
4.851.123 ₫ total
includes taxes & fees
8 Oct - 9 Oct
Meublé Il Riccio
Front of property – evening/night

13. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 3.621.846 ₫
4.074.564 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Abbadia Sicille Relais
Exterior

14. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (140 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 3.549.241 ₫
4.024.847 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Bed & Breakfast Vicolo dell'Oste
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

15. 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 2.971.167 ₫
3.388.995 ₫ total
includes taxes & fees
4 Oct - 5 Oct
DormiVeglia B&B
Property entrance

16. 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 2.206.786 ₫
2.548.176 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Residenza Fabroni
Suite Aria | Terrace/patio

17. 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 5.622.171 ₫
6.305.101 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Delcorto Suites
Panoramic Cottage, 1 Bedroom | Exterior

18. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (65 reviews)
"I had a fantastic experience with this place. Great people!!!"
South Korea
Young Rok
The price is 2.925.899 ₫
3.969.922 ₫ total
includes taxes & fees
7 Oct - 8 Oct
Affitacamere Maria Gabriella
Interior

19. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is 2.370.349 ₫
2.728.096 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Villa Fontis Rapolano
Outdoor pool

20. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (319 reviews)
"Breakfast was not impressive and very warm room with mosquitoes"
Canada
Baudouin
The price is 5.481.432 ₫
6.240.821 ₫ total
includes taxes & fees
18 Sept - 19 Sept
TH Perugia - Castello di Monterone
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

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."
Patricia 1-night trip
Posted 3 hours ago
Il Falconiere - Relais e Chateaux

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 166 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.