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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Cortona holiday rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

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 3.563.798 ₫
4.035.906 ₫ total
includes taxes & fees
14 Oct - 15 Oct
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 5.917.895 ₫
6.553.082 ₫ total
includes taxes & fees
11 Nov - 12 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 2.582.337 ₫
2.956.300 ₫ total
includes taxes & fees
15 Oct - 16 Oct
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 2.886.126 ₫
3.290.467 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Vicolo Della Scala Rooms - Il Sole
A modern kitchen with wooden cabinets, a microwave, and a black countertop.

5. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 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 1.656.952 ₫
2.328.963 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Limehome Arezzo Duomo
Room

6. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
The price is 2.130.573 ₫
2.517.225 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Bibi Boutique
Pool

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 2.177.906 ₫
2.569.291 ₫ total
includes taxes & fees
5 Nov - 6 Nov
iConic Wellness Resort
A crowded restaurant with brick walls and multiple tables and chairs.

8. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (150 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 4.497.522 ₫
5.063.004 ₫ total
includes taxes & fees
3 Nov - 4 Nov
La Locanda di San Francesco
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

9. 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 3.629.686 ₫
4.108.383 ₫ total
includes taxes & fees
14 Oct - 15 Oct
San Michele al Borgo
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

10. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is 7.292.946 ₫
8.137.969 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Fontelunga Hotel & Villas
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

11. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (135 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 5.965.310 ₫
6.677.570 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Il Tosco
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

12. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (162 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is 3.310.747 ₫
3.815.415 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio
An interior courtyard with stone columns, arches, and a mosaic.

13. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 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 4.122.850 ₫
4.650.864 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Meublé Il Riccio
A spa area with a stone-walled arch, a hot tub, and a small window.

14. 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 2.848.514 ₫
3.249.094 ₫ total
includes taxes & fees
8 Nov - 9 Nov
DormiVeglia B&B
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

15. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 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 2.722.383 ₫
3.110.350 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Bed & Breakfast Vicolo dell'Oste
A courtyard with a pool, stone benches, and a view of a hill.

16. 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 5.775.934 ₫
6.556.054 ₫ total
includes taxes & fees
24 Oct - 25 Oct
TH Perugia - Castello di Monterone
A modern hotel room with large windows, a bed, a desk, and a chair.

17. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (82 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 1.954.608 ₫
2.323.663 ₫ total
includes taxes & fees
3 Nov - 4 Nov
B&B 52cento
A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (48 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is 4.899.970 ₫
5.505.812 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Delcorto Suites
An arched doorway leading to a building with a wooden door and a staircase.

19. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 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 2.040.949 ₫
2.360.773 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Residenza Fabroni
A patio area with outdoor seating, potted plants, and a view of the landscape.

20. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is 2.805.115 ₫
3.806.040 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Affitacamere Maria Gabriella
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
"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"
lise 1-night trip
Posted 1 hour 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.