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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Cortona holiday rentals

Deluxe Apartment, City View | Soundproofing, iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ฿4,660
฿5,240 total
includes taxes & fees
4 Jul - 5 Jul
CASA AMBRA
Lobby

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 ฿4,334
฿4,919 total
includes taxes & fees
5 Jul - 6 Jul
B&B Piccolo Hotel
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ฿3,788
฿4,318 total
includes taxes & fees
3 Jul - 4 Jul
Vicolo Della Scala Rooms - Il Sole
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ฿3,389
฿3,880 total
includes taxes & fees
3 Jul - 4 Jul
Vicolo Della Scala Rooms - La Luna
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (111 reviews)
"It was very well located ."
Canada
Marlenne
The price is ฿5,411
฿6,104 total
includes taxes & fees
2 Jul - 3 Jul
Meublé Il Riccio
Exterior

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 ฿3,501
฿4,003 total
includes taxes & fees
2 Jul - 3 Jul
Bed & Breakfast Vicolo dell'Oste
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (189 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is ฿3,003
฿3,531 total
includes taxes & fees
19 Jul - 20 Jul
Cameracaffè Centro
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (91 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ฿6,278
฿7,058 total
includes taxes & fees
15 Jul - 16 Jul
Casanova - Panoramic Rooms and Suites
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (42 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is ฿9,346
฿10,432 total
includes taxes & fees
2 Jul - 3 Jul
Castello di Gargonza
BBQ/picnic Area

Residenza d'epoca Ca' de Principi

Residenza d'epoca Ca' de Principi
Piegaro
9.8 out of 10, Exceptional, (13 reviews)
"The hotel was charming, and the staff really nice. Breakfast had lots of options. The room was large and beautiful view of the hills. The bed was comfortable."
United States
Robyn
The price is ฿4,487
฿4,936 total
includes taxes & fees
2 Jul - 3 Jul
Residenza d'epoca Ca' de Principi
Outdoor pool, pool loungers

TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (315 reviews)
"Stunning property, beautiful views"
United Kingdom
Liam
The price is ฿6,897
฿7,852 total
includes taxes & fees
16 Jul - 17 Jul
TH Perugia - Castello di Monterone
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿5,250
฿5,889 total
includes taxes & fees
2 Jul - 3 Jul
Abbadia Sicille Relais
Bar (on property)

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 ฿4,033
฿4,513 total
includes taxes & fees
2 Jul - 3 Jul
La Piccola Locanda
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (4 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is ฿4,054
฿4,612 total
includes taxes & fees
5 Jul - 6 Jul
PienzaLettings Suites
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 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 ฿5,792
฿6,523 total
includes taxes & fees
3 Jul - 4 Jul
Delcorto Suites
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (148 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is ฿7,181
฿8,127 total
includes taxes & fees
22 Jul - 23 Jul
Hotel San Gregorio
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is ฿15,188
฿16,859 total
includes taxes & fees
27 Jul - 28 Jul
L'Olmo
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (145 reviews)
"Great location."
United States
James
The price is ฿4,832
฿5,468 total
includes taxes & fees
16 Jul - 17 Jul
La Locanda di San Francesco
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is ฿2,755
฿3,106 total
includes taxes & fees
2 Jul - 3 Jul
Artisti del Cavallo Tourism
Couples treatment room(s), sauna, hot tub, steam room, body treatments

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (47 reviews)
"Our stay was great. "
United States
Elena
The price is ฿3,287
฿3,768 total
includes taxes & fees
2 Jul - 3 Jul
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
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

Hotel San Luca

Hotel San Luca

10/10 Excellent
"Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona"
Mariusz 1-night trip
Posted 1 day ago
Hotel San Luca

Find out more about Cortona

Search for holiday rentals in Cortona on Expedia! You can easily find your home rentals, villas, holiday 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 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 143 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 Casali Palace 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.