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
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Cortona holiday rentals

Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (22 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 3.490.069 ₫
3.961.388 ₫ total
includes taxes & fees
5 Jul - 6 Jul
B&B Piccolo Hotel
Deluxe Apartment, City View | Iron/ironing board, free WiFi

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 3.752.662 ₫
4.219.662 ₫ total
includes taxes & fees
5 Jul - 6 Jul
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 3.050.301 ₫
3.477.643 ₫ total
includes taxes & fees
8 Jun - 9 Jun
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 2.729.231 ₫
3.124.466 ₫ total
includes taxes & fees
9 Jun - 10 Jun
Vicolo Della Scala Rooms - La Luna
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (103 reviews)
"Place is amazing and maintained perfectly."
United States
Dominic
The price is 4.362.985 ₫
4.921.754 ₫ total
includes taxes & fees
12 Jun - 13 Jun
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, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is 3.131.429 ₫
3.628.277 ₫ total
includes taxes & fees
15 Jun - 16 Jun
iConic Wellness Resort
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 2.588.566 ₫
3.031.127 ₫ total
includes taxes & fees
27 Jun - 28 Jun
Cameracaffè Centro
Outdoor pool, pool loungers

Castello di Monterone

Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (313 reviews)
"Absolutely beautiful location, friendly and helpful staff, and wonderfully memorable experience! The bar tender was so kind and we loved our room and the views around the castello!"
United States
Shauna
The price is 6.104.493 ₫
6.928.988 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Castello di Monterone
Suite, Multiple Beds, Valley View | Bathroom | Shower, rainfall showerhead, designer toiletries, hair dryer

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (142 reviews)
"Great location."
United States
James
The price is 4.258.580 ₫
4.806.908 ₫ total
includes taxes & fees
11 Jun - 12 Jun
La Locanda di San Francesco
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 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 5.178.700 ₫
5.819.004 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Delcorto Suites
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 5.711.545 ₫
6.374.552 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Abbadia Sicille Relais
Interior

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
The price is 2.526.860 ₫
2.901.858 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Villa Fontis Rapolano
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (145 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.586.792 ₫
6.329.176 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Hotel San Gregorio
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 2.026.612 ₫
2.351.585 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Residenza Fabroni
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 3.618.369 ₫
3.980.267 ₫ total
includes taxes & fees
6 Jun - 7 Jun
Residenza d'epoca Ca' de Principi
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (137 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 3.600.917 ₫
4.083.448 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Bed & Breakfast Vicolo dell'Oste
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (88 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
The price is 5.056.082 ₫
5.684.155 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Casanova - Panoramic Rooms and Suites
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 3.889.111 ₫
4.400.492 ₫ total
includes taxes & fees
10 Jun - 11 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 2.864.717 ₫
3.273.658 ₫ total
includes taxes & fees
7 Jun - 8 Jun
DormiVeglia B&B
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (122 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 8.714.414 ₫
9.708.167 ₫ total
includes taxes & fees
9 Jun - 10 Jun
Il Tosco
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 San Michele

Hotel San Michele

8/10 Good
"The location is fantastic. Just steps from the shopping and restaurants. The hotel is old fashioned and charming. The bathrooms are in need of an upgrade both fixtures and lighting. But it’s quirky ways also are the very thing that makes it charming. I would ask for a room furthest away from Via Nationale as that street can be loud at night. They have a nice breakfast each morning w an option to eat in the outdoor courtyard. Their sweet staff will bring you speciality coffees to enjoy!"
Susannah 5-night trip
Posted 19 hours ago
Hotel San Michele

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 140 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.