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

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Cortona holiday rentals

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 3.706.059 ₫
4.196.540 ₫ total
includes taxes & fees
25 Jul - 26 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 2.992.523 ₫
3.411.771 ₫ total
includes taxes & fees
27 Jul - 28 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 2.677.535 ₫
3.065.283 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Vicolo Della Scala Rooms - La Luna
Interior

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 4.274.838 ₫
4.822.317 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Meublé Il Riccio
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 4.119.040 ₫
4.650.971 ₫ total
includes taxes & fees
6 Aug - 7 Aug
La Locanda di San Francesco
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (38 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 3.903.741 ₫
4.474.156 ₫ total
includes taxes & fees
26 Jul - 27 Jul
iConic Wellness Resort
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 2.963.678 ₫
3.380.041 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Bed & Breakfast Vicolo dell'Oste
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (151 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 6.186.812 ₫
6.985.594 ₫ total
includes taxes & fees
6 Aug - 7 Aug
Hotel San Gregorio
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 2.372.610 ₫
2.789.894 ₫ total
includes taxes & fees
3 Aug - 4 Aug
Cameracaffè Centro
Outdoor pool, pool loungers

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 5.303.028 ₫
6.043.378 ₫ total
includes taxes & fees
25 Jul - 26 Jul
TH Perugia - Castello di Monterone
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (38 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 4.598.171 ₫
5.177.983 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Delcorto Suites
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

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 3.342.146 ₫
3.796.356 ₫ total
includes taxes & fees
25 Jul - 26 Jul
DormiVeglia B&B
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

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 2.027.493 ₫
2.410.235 ₫ total
includes taxes & fees
30 Jul - 31 Jul
B&B 52cento
Exterior

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 3.763.493 ₫
4.259.837 ₫ total
includes taxes & fees
28 Jul - 29 Jul
San Michele al Borgo
Terrace/patio

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 6.356.716 ₫
7.082.409 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Abbadia Sicille Relais
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (129 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 6.322.669 ₫
7.074.931 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Il Tosco
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 3.545.265 ₫
3.899.852 ₫ total
includes taxes & fees
23 Jul - 24 Jul
Residenza d'epoca Ca' de Principi
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 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 2.116.188 ₫
2.447.801 ₫ total
includes taxes & fees
30 Jul - 31 Jul
Residenza Fabroni
Exterior

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is 3.081.701 ₫
3.389.871 ₫ total
includes taxes & fees
27 Jul - 28 Jul
Locanda Antico Borgo
Junior Suite | Terrace/patio

Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is 3.513.232 ₫
3.984.582 ₫ total
includes taxes & fees
13 Aug - 14 Aug
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

Hotel San Luca

Hotel San Luca

10/10 Excellent
"This is a great deal for a stay in Cortona Tough wi fi but it really didn’t matter because the place was great"
Brian 2-night trip
Posted 2 days ago
Hotel San Luca

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 152 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 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.