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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Cortona holiday rentals

Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 3.506.453 ₫
3.979.984 ₫ total
includes taxes & fees
7 Jun - 8 Jun
B&B Piccolo Hotel
Deluxe Apartment, City View | Iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 6.266.120 ₫
6.984.636 ₫ total
includes taxes & fees
1 Jun - 2 Jun
CASA AMBRA
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.742.044 ₫
3.139.135 ₫ total
includes taxes & fees
22 May - 23 May
Vicolo Della Scala Rooms - La Luna
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is 3.055.954 ₫
3.484.088 ₫ total
includes taxes & fees
1 Jun - 2 Jun
Vicolo Della Scala Rooms - Il Sole
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, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 3.142.084 ₫
3.640.623 ₫ total
includes taxes & fees
25 May - 26 May
iConic Wellness Resort
Courtyard

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (96 reviews)
"Loved it!"
United States
Michael
The price is 4.377.830 ₫
4.938.499 ₫ total
includes taxes & fees
26 May - 27 May
Meublé Il Riccio
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (138 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is 5.027.285 ₫
5.652.899 ₫ total
includes taxes & fees
11 Jun - 12 Jun
La Locanda di San Francesco
22-inch TV with digital channels

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (134 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 3.613.169 ₫
4.097.341 ₫ total
includes taxes & fees
26 May - 27 May
Bed & Breakfast Vicolo dell'Oste
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 3.620.413 ₫
3.982.516 ₫ total
includes taxes & fees
20 May - 21 May
Residenza d'epoca Ca' de Principi
Outdoor pool, pool loungers

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (310 reviews)
"Beautiful hotel in restored castle. Staff were kind and welcoming. "
United Kingdom
Stuart
The price is 5.580.162 ₫
6.353.229 ₫ total
includes taxes & fees
26 May - 27 May
Castello di Monterone
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (175 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 5.188.299 ₫
5.799.155 ₫ total
includes taxes & fees
28 May - 29 May
Abbadia Sicille Relais
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (184 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 2.422.901 ₫
2.849.030 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Cameracaffè Centro
Front of property

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (142 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.176.592 ₫
5.878.581 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Hotel San Gregorio
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is 1.741.916 ₫
1.916.108 ₫ total
includes taxes & fees
20 May - 21 May
L'Antica Sosta
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is 3.271.054 ₫
3.720.698 ₫ total
includes taxes & fees
20 May - 21 May
PienzaLettings Suites
Camera Superior, vista città, primo piano senza ascensore | Laptop workspace, iron/ironing board, free WiFi

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is 2.819.713 ₫
3.224.223 ₫ total
includes taxes & fees
20 May - 21 May
TuscanyLettings Studio&Room
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (36 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 5.232.030 ₫
5.878.119 ₫ total
includes taxes & fees
24 May - 25 May
Delcorto Suites
Breakfast area

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 3.147.023 ₫
3.461.725 ₫ total
includes taxes & fees
20 May - 21 May
Locanda Antico Borgo
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (101 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is 2.411.686 ₫
2.775.740 ₫ total
includes taxes & fees
2 Jun - 3 Jun
Residenza Fabroni
Exterior

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.4 out of 10, Exceptional, (6 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
The price is 3.759.495 ₫
4.135.383 ₫ total
includes taxes & fees
21 May - 22 May
La Locanda Di Cetona
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
"The property is beautiful, the spa is great and most importantly the bed and Bedding were fabulous! The rooms are large and very nicely appointed with a sense of calm and quiet. The staff very attentive and dedicated to our overall stay and well being! Alessandro in the restaurant & Simone,; Anna, Sara, Matilde at the front desk, Paula in the Spa and the valet staff helping with garage parking and luggage! Worth spending several days! . Dining was superior, fine dining at its best and delicious by Chef Michele!! COMPLEMENTI !!! The Omlies"
Samantha 1-night trip
Posted 2 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 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 Signorelli Theatre and Museum of the Etruscan Academy, 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.