Search Holiday Rentals in Cortona

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

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 3.516.410 ₫
3.991.286 ₫ total
includes taxes & fees
18 May - 19 May
B&B Piccolo Hotel
Deluxe Apartment, City View | Iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 6.301.734 ₫
7.024.335 ₫ total
includes taxes & fees
10 May - 11 May
CASA AMBRA
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is 3.073.323 ₫
3.503.890 ₫ total
includes taxes & fees
14 May - 15 May
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 2.749.830 ₫
3.148.048 ₫ total
includes taxes & fees
18 May - 19 May
Vicolo Della Scala Rooms - La Luna
Exterior detail

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is 3.405.734 ₫
3.807.925 ₫ total
includes taxes & fees
10 May - 11 May
Il Rifugio del Borgo
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (94 reviews)
"An amazingly beautiful and historic property. Our room had an incredible view. The staff was fantastic- welcoming and helpful. The location is spectacular. I highly recommend. "
United States
Hallie
The price is 4.390.261 ₫
4.952.522 ₫ total
includes taxes & fees
14 May - 15 May
Meublé Il Riccio
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 2.607.109 ₫
3.053.432 ₫ total
includes taxes & fees
18 May - 19 May
iConic Wellness Resort
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (141 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.212.610 ₫
5.919.483 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Hotel San Gregorio
Outdoor pool, pool loungers

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (309 reviews)
"Beautiful hotel in restored castle. Staff were kind and welcoming. "
United Kingdom
Stuart
The price is 5.467.124 ₫
6.230.384 ₫ total
includes taxes & fees
14 May - 15 May
Castello di Monterone
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 3.618.500 ₫
4.103.584 ₫ total
includes taxes & fees
20 May - 21 May
PienzaLettings Suites
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (137 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 6.102.620 ₫
6.836.623 ₫ total
includes taxes & fees
10 May - 11 May
La Locanda di San Francesco
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is 3.638.309 ₫
4.125.850 ₫ total
includes taxes & fees
18 May - 19 May
Bed & Breakfast Vicolo dell'Oste
Monolocale Exclusive, vista città, secondo 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 2.847.384 ₫
3.255.863 ₫ total
includes taxes & fees
2 Jun - 3 Jun
TuscanyLettings Studio&Room
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 3.640.990 ₫
4.005.151 ₫ total
includes taxes & fees
20 May - 21 May
Residenza d'epoca Ca' de Principi
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"The room was really clean and as described. Unfortunately, the hotel restaurant was closed and that was not mentioned on the site. I learned about it the day before my arrival. Fortunately, the host had good restaurant suggestions. The hotel advertise a pool and a jacuzzi, they have both but the pool was VERY cold (normal in April) and the jacuzzi was not inviting (bee nest, Luke warm, in the shade...). Concerning the breakfast, note that it is not a buffet, a box get delivered to your room. You...
Canada
Chantal
The price is 4.940.619 ₫
5.527.108 ₫ total
includes taxes & fees
14 May - 15 May
Abbadia Sicille Relais
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 4.388.536 ₫
4.951.131 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
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, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.537.463 ₫
2.914.950 ₫ total
includes taxes & fees
13 May - 14 May
DormiVeglia B&B
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 3.272.740 ₫
3.661.632 ₫ total
includes taxes & fees
10 May - 11 May
La Piccola Locanda
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (119 reviews)
"Exceptional place! Spacious and very comfortable. The breakfasts were magnificent and the owner and management so accommodating. Highly recommend. "
United States
Shane
The price is 8.130.848 ₫
9.067.167 ₫ total
includes taxes & fees
10 May - 11 May
Il Tosco
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (182 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 2.502.953 ₫
2.938.860 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Cameracaffè Centro
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"Franz and Manuela are amazing. They’re friendly and helpful. The location is perfect! Two doors down from the main palazzo and the main street: Via Nazionale. If arriving by train, take the small bus to Palazzo Garibaldi. The bigger bus stops further down the mountain at Mercato and it is quite an uphill hike."
Andrew 3-night trip
Posted 4 hours ago
Hotel Italia

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 145 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.