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Our top choices for Cortona holiday rentals

Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8)
"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
La Piccola Locanda

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is 3.088.401 ₫
3.520.777 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Bed & Breakfast Vicolo dell'Oste

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is 6.974.171 ₫
7.795.124 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Il Tosco

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is 1.834.510 ₫
2.017.961 ₫ total
includes taxes & fees
17 Dec - 18 Dec
L'Antica Sosta

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is 3.790.395 ₫
4.169.342 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Locanda del Viandante

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is 6.794.482 ₫
7.628.350 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Albergo Diffuso Borgo Santo

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is 2.240.494 ₫
2.526.311 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Artisti del Cavallo Tourism

Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.6 out of 10, Exceptional, (38)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
The price is 2.751.485 ₫
3.397.241 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Sarna Residence

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is 5.430.953 ₫
6.159.507 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

THE MONNA LISA RESORT

THE MONNA LISA RESORT
Arezzo
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is 3.284.935 ₫
3.798.733 ₫ total
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT

Welchome suites

Welchome suites
Old Town Perugia
9.2 out of 10, Wonderful, (15)
"Great location and host was extremely helpful and quick to communicate. "
United States
Jenifer
The price is 2.419.608 ₫
2.754.221 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Welchome suites

Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
Dolce Rosa Centro Storico

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 1.920.424 ₫
2.205.119 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Abbadia Sicille Relais

Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is 3.374.078 ₫
3.773.253 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Borgo Dolciano

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is 4.733.845 ₫
5.330.766 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Delcorto Suites

La Murata

La Murata
Rapolano Terme
9.0 out of 10, Wonderful, (11)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is 3.941.923 ₫
4.459.652 ₫ total
includes taxes & fees
17 Dec - 18 Dec
La Murata
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

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 146 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.