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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 4.183.228 ₫
4.722.716 ₫ total
includes taxes & fees
12 Aug - 13 Aug
B&B Piccolo Hotel
Apartment (1 Bedroom) | Front of property

2. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.703.636 ₫
3.095.165 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Vicolo Della Scala Rooms - La Luna
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 3.021.694 ₫
3.445.028 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Vicolo Della Scala Rooms - Il Sole
Interior

4. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (115 reviews)
"It was very well located ."
Canada
Marlenne
The price is 4.316.509 ₫
4.869.325 ₫ total
includes taxes & fees
11 Aug - 12 Aug
Meublé Il Riccio
Food court

5. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (146 reviews)
"Lucca was the perfect host, very accommodating to any queries we had and was always willing to help during our stay Couldn’t recommend staying here highly enough - we had a great time staying here and would highly recommend if you are in the area definitely book here"
United Kingdom
Jonathan
The price is 3.690.086 ₫
4.180.259 ₫ total
includes taxes & fees
27 Aug - 28 Aug
La Locanda di San Francesco
Porch

6. 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 2.395.739 ₫
2.817.091 ₫ total
includes taxes & fees
28 Aug - 29 Aug
Cameracaffè Centro
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (39 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 3.098.073 ₫
3.589.629 ₫ total
includes taxes & fees
7 Sept - 8 Sept
iConic Wellness Resort
Exterior

8. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (139 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 3.135.149 ₫
3.569.829 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Bed & Breakfast Vicolo dell'Oste
Terrace/patio

9. 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 5.345.015 ₫
5.970.390 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Abbadia Sicille Relais
Suite Aria | Terrace/patio

10. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (40 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is 4.617.220 ₫
5.200.107 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Delcorto Suites
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

11. 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 3.374.726 ₫
3.833.363 ₫ total
includes taxes & fees
12 Aug - 13 Aug
DormiVeglia B&B
Property entrance

12. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (130 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 7.494.618 ₫
8.365.245 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Il Tosco
Food and drink

13. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.768.427 ₫
6.527.017 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Hotel San Gregorio
Seasonal outdoor pool, pool loungers

14. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (316 reviews)
"Breakfast buffet was outstanding."
United States
Larraine
The price is 5.502.001 ₫
6.264.240 ₫ total
includes taxes & fees
11 Aug - 12 Aug
TH Perugia - Castello di Monterone
Bar (on property)

15. La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is 3.217.762 ₫
3.600.121 ₫ total
includes taxes & fees
10 Aug - 11 Aug
La Piccola Locanda
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

16. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (81 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 2.141.058 ₫
2.536.912 ₫ total
includes taxes & fees
19 Aug - 20 Aug
B&B 52cento
Courtyard

17. 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 8.556.107 ₫
9.532.883 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Fontelunga Hotel & Villas
Exterior

18. 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 3.800.181 ₫
4.301.364 ₫ total
includes taxes & fees
10 Aug - 11 Aug
San Michele al Borgo
Property entrance

19. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (104 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 2.043.304 ₫
2.368.799 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Residenza Fabroni
Junior Suite | Terrace/patio

20. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is 3.122.881 ₫
3.556.334 ₫ total
includes taxes & fees
7 Sept - 8 Sept
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
"Everything was absolutely perfect and we would happily go back."
Haim 3-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 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 Signorelli Theatre and Museum of the Etruscan Academy, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Santa Maria Nuova 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.