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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 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 3.361.477 ₫
3.821.188 ₫ 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 6.318.490 ₫
7.043.011 ₫ total
includes taxes & fees
4 May - 5 May
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 2.757.141 ₫
3.156.418 ₫ total
includes taxes & fees
6 May - 7 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 3.081.494 ₫
3.513.207 ₫ total
includes taxes & fees
5 May - 6 May
Vicolo Della Scala Rooms - Il Sole
Exterior detail

Il Rifugio del Borgo

Il Rifugio del Borgo
Città della Pieve
The price is 3.414.789 ₫
3.818.050 ₫ total
includes taxes & fees
4 May - 5 May
Il Rifugio del Borgo
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 2.603.350 ₫
3.049.030 ₫ total
includes taxes & fees
4 May - 5 May
iConic Wellness Resort
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 3.633.063 ₫
4.119.901 ₫ total
includes taxes & fees
10 May - 11 May
Bed & Breakfast Vicolo dell'Oste
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 5.459.016 ₫
6.221.091 ₫ total
includes taxes & fees
18 May - 19 May
Castello di Monterone
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 5.155.669 ₫
5.763.908 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Abbadia Sicille Relais
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
The price is 6.082.391 ₫
6.875.975 ₫ total
includes taxes & fees
10 May - 11 May
Hotel San Gregorio
Front of property

Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (37 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is 2.934.622 ₫
3.351.647 ₫ total
includes taxes & fees
4 May - 5 May
Residence al Lago
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (137 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is 6.178.153 ₫
6.919.532 ₫ total
includes taxes & fees
10 May - 11 May
La Locanda di San Francesco
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (93 reviews)
"Nothing negative could be said about this absolutely fabulous property. Great staff, great location, best room of our 22 day, 11 stop trip. Easy luggage so off, great everything. We will be back and will definitely stay here again. "
United States
Michael
The price is 4.401.934 ₫
4.965.690 ₫ total
includes taxes & fees
14 May - 15 May
Meublé Il Riccio
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 2.533.804 ₫
2.910.747 ₫ total
includes taxes & fees
4 May - 5 May
DormiVeglia B&B
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 3.650.671 ₫
4.015.800 ₫ total
includes taxes & fees
20 May - 21 May
Residenza d'epoca Ca' de Principi
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (181 reviews)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is 2.555.509 ₫
2.996.405 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Cameracaffè Centro
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 3.719.032 ₫
4.214.499 ₫ total
includes taxes & fees
5 May - 6 May
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (99 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is 2.442.768 ₫
2.810.608 ₫ total
includes taxes & fees
25 May - 26 May
Residenza Fabroni
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 1.751.506 ₫
1.926.657 ₫ total
includes taxes & fees
4 May - 5 May
L'Antica Sosta
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is 5.231.660 ₫
5.878.513 ₫ total
includes taxes & fees
10 May - 11 May
Delcorto Suites
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
"Incredible place. History, attention to details, ambiance, food - just perfection!"
VICTORIA 2-night trip
Posted 9 hours 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 Giuseppe Garibaldi Memorial 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.