The 10 best holiday rentals in Cortona, Italy | Booking.com
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Holiday Rentals in Cortona

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The best holiday rentals in Cortona

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Casa Dreosti

Cortona Old Town, Cortona

Set within 32 km of Piazza Grande and 38 km of Terme di Montepulciano, Casa Dreosti offers rooms with air conditioning and a private bathroom in Cortona.

E
Emma
From
United Kingdom
Casa Dreosti was a true gem. The owner and host, Jeroen, was friendly and engaging, and we loved meeting his gorgeous dogs, Judy and Lucy. The room was large, beautifully decorated, and the shower was powerful and spacious, with stunning tiling. We also appreciated having access to a washing machine, and thanks to the washing line just outside the windows, our clothes dried within a couple of hours in the August heat. The highlight of our stay was definitely the breakfast. Jeroen, a true foodie, bakes fresh croissants every morning and serves them with seasonal fresh fruit or a smoothie/juice, depending on what’s available that day. Each morning, we enjoyed sitting outside on the charming Cortona street, surrounded by plants and flowers in front of Casa Dreosti. It’s such a special memory for us, and we will definitely return when we visit Cortona again.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 213 reviews
Price from
£105.70
1 night, 2 adults

La Renaia

Cortona

Featuring a seasonal outdoor swimming pool and views of mountain, La Renaia is a farm stay situated in a historic building in Cortona, 33 km from Piazza Grande.

B
Barbara
From
United Kingdom
Carola was a lovely host who went out of her way to accommodate us. Plus the swimming pool was fabulous. And the surroundings and walks were beautiful and Cortona was very near. Our accommodation was very spacious and well equipped and clean.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 228 reviews
Price from
£75.81
1 night, 2 adults

Casa del Loggiato

Cortona Old Town, Cortona

Set in Cortona, 32 km from Piazza Grande and 37 km from Terme di Montepulciano, Casa del Loggiato offers accommodation with free WiFi in a historic building.

N
Nelda
From
South Africa
Beautiful apartment giving us a real 'Tuscan' feel. Wish we could stay longer to enjoy the apartment. Location is perfect!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 148 reviews
Price from
£90.97
1 night, 2 adults

Villa Augusto

Cortona

Located within 32 km of Piazza Grande and 50 km of Perugia Cathedral, Villa Augusto provides rooms with air conditioning and a private bathroom in Cortona.

M
Monika
From
Germany
The villa is a rare gem, as is the host and his wonderful family. The patina of a bygone era envelopes the visitor as you enter the marvelous rooms filled with antique furniture and original floors and walls, designed for a noble family. The garden is really a park, peaceful and romantic, and a walk to Cortona leads through fields of wild Irises framing the olive groves. The host is a true connoisseur of his city and surroundings and has fantastic recommendations and shares them freely, taking his time to explain everything in detail. Every minute was enjoyable and we plan on coming back for a longer stretch to this wonderful corner of Italy.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 118 reviews
Price from
£136.02
1 night, 2 adults

Le Residenze Ristori

Cortona Old Town, Cortona

Set in a 17th-century building, Le Residenze Ristori offers self-catering apartments and rooms with free WiFi in the historic centre of Cortona.

r
redguy41
From
Croatia
Absolutely charming, amazing little room with a beautiful view, quiet, well-equipped and cosy. The only thing missing would be a fireplace! It's maybe 5 minutes on foot to the piazza in the centre. The bed was super comfy, and all the amenities are there, even a small Dolce Gusto coffee machine. Very warm as well in the winter, the heating was great! Tall people might have a bit of a problem in the attic room, but - duck! :) The host was there to give us the keys and communicated well through WhatsApp and even granted us a late check-out because of our train. Strongly recommended!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 860 reviews
Price from
£66.71
1 night, 2 adults

Agriturismo San Francesco

Cortona

Set within 29 km of Piazza Grande and 32 km of Terme di Montepulciano, Agriturismo San Francesco offers rooms with air conditioning and a private bathroom in Cortona.

J
John
From
Switzerland
Very comfortable, clean room in a traditional building in beautiful surroundings. The owner is very friendly and the breakfast was superb, the best we had on the whole trip. Overall, fantastic value for money and we would definitely recommend!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 433 reviews
Price from
£95.30
1 night, 2 adults

Dolce Maria

Cortona Old Town, Cortona

Just 100 metres from Piazza della Repubblica, the Dolce Maria is located in the mediaeval hill town of Cortona.

A
Andrea
From
Czech Republic
Very pleasant accommodation, nice old house. There is the restaurant in the house, food was great. The breakfast was delicious, every food is home- made. The owner was very friendly.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 416 reviews
Price from
£103.10
1 night, 2 adults

Locanda Petrella

Cortona Old Town, Cortona

With a quiet location in Cortona's pedestrian area, Locanda Petrella is a 5-minute walk from Cortona Cathedral. It is set on the second floor of a historic building dating back to the 1800s.

S
S
From
United Kingdom
Very nice atmosphere. The room was feel you are in the real Tuscany! Well organised. Owner/runner was very friendly. No tv which was a plus for us.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 389 reviews
Price from
£116.09
1 night, 2 adults

Monastero San Silvestro

Cortona

Set within 32 km of Piazza Grande and 49 km of Perugia Cathedral, Monastero San Silvestro provides rooms with air conditioning and a private bathroom in Cortona.

S
Sofia
From
Brazil
everything is AMAZING! so confortable, the staff is absolutely lovely (super accessible on WhatsApp at all times!!!) and the bed and the sheets are just dreamy! We would 100% come back!!! The kitchen is great, we cooked a lot with fresh ingredients from the supermarket nearby! amazing!
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 341 reviews
Price from
£111.67
1 night, 2 adults

Agrisalotto

Cortona

Boasting an infinity pool and views of pool, Agrisalotto is a farm stay set in a historic building in Cortona, 30 km from Piazza Grande.

T
Topolski
From
Poland
A beautiful, picturesque and charming place in the heart of Tuscany... a real paradise for relaxation. Very nice, professional service and staff. I recommend staying in such a charming place to everyone. We will definitely come back here ❤️
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 132 reviews
Price from
£108.30
1 night, 2 adults
All holiday rentals in Cortona

Most booked holiday rentals in Cortona and surroundings in the past month

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Highly rated holiday rentals in Cortona and nearby

  • La Casa di Iole

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.1
    Very good - What previous guests thought, 34 reviews

    Set in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, La Casa di Iole offers accommodation with free WiFi in a historic building.

  • Démodé

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 45 reviews

    Démodé is situated in the Cortona Old Town district of Cortona, 38 km from Terme di Montepulciano, 47 km from Perugia Train Station and 49 km from Corso Vannucci.

  • Casa Ambra

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 59 reviews

    Located in Cortona, 30 km from Piazza Grande, Casa Ambra has free bikes, private parking and rooms with free WiFi access.

  • B&B Piccolo Hotel

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 253 reviews

    Located in Cortona, 30 km from Piazza Grande, B&B Piccolo Hotel features accommodation with spa facilities and wellness packages.

  • Casa Teatro

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 29 reviews

    Set in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station, Casa Teatro offers air conditioning.

  • SIGNORELLI HOUSE

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 8 reviews

    Offering city views, SIGNORELLI HOUSE is an accommodation located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station.

  • B&B San Francesco

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 456 reviews

    Located in Cortona, 31 km from Piazza Grande and 37 km from Terme di Montepulciano, B&B San Francesco provides accommodation with free WiFi in a historic building.

  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 43 reviews

    Situated in Cortona, 31 km from Piazza Grande and 37 km from Terme di Montepulciano, Cortona's Rooftop Nest features accommodation with free WiFi in a historic building.

Enjoy breakfast in Cortona and nearby

  • Casa Kita

    Cortona
    Breakfast options
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 227 reviews

    Featuring mountain views, Casa Kita offers accommodation with terrace, around 31 km from Piazza Grande. With lake views, this accommodation provides a patio. The guest house features family rooms.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 104 reviews

    Set in Cortona, 33 km from Piazza Grande, Casale l'Antico Carro has pool with a view, parking on-site and rooms with free WiFi access.

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 68 reviews

    Nestled amid the hills on the Umbria - Tuscany border, the farm house is immersed in nature, just 6 km away from the historic town of Cortona.

  • Locanda Del Molino

    Cortona
    Breakfast options
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 387 reviews

    Locanda Del Molino is just a 10-minute drive from Cortona and features a typical restaurant where you can sample authentic cuisine from the region in a cosy atmosphere.

  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 57 reviews

    Featuring free WiFi, parking on-site and an infinity pool, the recently renovated property of Agriturismo Annibale, offers accommodation in Tuoro sul Trasimeno, 39 km from Perugia Cathedral and 40 km...

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 92 reviews

    Set in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, San Lazzo Luxury Room - ROOM & PERSONAL SPA offers air conditioning. A hot tub is available for guests.

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 49 reviews

    Featuring a spa bath, Tuttomio Suite con idromassaggio is located in Castiglion Fiorentino.

  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 236 reviews

    Set within 20 km of Piazza Grande and 44 km of Terme di Montepulciano, San Michele al Castello offers rooms with air conditioning and a private bathroom in Castiglion Fiorentino.

These holiday rentals in Cortona and nearby have options with free cancellation

  • La finestra sul Teatro

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 72 reviews

    Located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station, La finestra sul Teatro offers air conditioning.

  • Casa Vacanze Beppina Cortona

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 53 reviews

    Offering city views, Casa Vacanze Beppina Cortona is an accommodation set in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station. The property has quiet street views.

  • Cortona Shabby Chic House

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 64 reviews

    Set within the Cortona Old Town district in Cortona, Cortona Shabby Chic House has air conditioning, a balcony, and inner courtyard views.

  • Il Vicolino

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 54 reviews

    Featuring a spa bath, Il Vicolino is set in Cortona. Located in the Cortona Old Town district, the property provides guests with access to a hot tub.

  • B&B Il Rosmarino

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 20 reviews

    Offering a garden and lake view, B&B Il Rosmarino is located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station.

  • Agriturismo Il Torrino

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 8 reviews

    Set in Cortona, 31 km from Piazza Grande and 50 km from Perugia Cathedral, Agriturismo Il Torrino offers air conditioning.

  • MAGNOLIA

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 54 reviews

    Featuring garden views, MAGNOLIA provides accommodation with a garden and a patio, around 38 km from Terme di Montepulciano.

  • Il Centrale

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 221 reviews

    Il Centrale is situated in Cortona, 30 km from Piazza Grande, 50 km from Perugia Cathedral, and 50 km from San Severo Church - Perugia.

FAQ about holiday rentals in Cortona

Holiday rentals that guests love in Cortona

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  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 11 reviews
    We really enjoyed our stay im this charmimg Tuscan country house. The pool was clean and we had a lot of fun swimming in it. Luca and his family were really nice and even organized our participation at a local dinner party in the nearby village of Ronzano with typical Tuscan meals. Thank you also for the present of two bottles of local wine at the end of our stay. We would definitely like to come Back.
    Guest review by
    beate
    Family with young children
  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 78 reviews
    Christina was very hospitable and we loved the decor, location and history of the old renovated Italian villa, dipped in charm and the sound of a church bell in the distance.
    Guest review by
    Heather
    Family with young children
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 4 reviews
    Fantastic small villa for a family of 4 or 2 couples. Very quiet location in the countryside near Cortona with a view on the mountains. Ideal spot to go and check the central part of Tuscany. Villa has a great pool and garden. House is cosy, but has everything you need.
    Guest review by
    Ben
    Family with young children
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 90 reviews
    The villa we stayed in was classic and beautiful. Each room had its own bathroom, providing ample space for everyone. The kitchen was well-furnished with all the necessary amenities. The garden was stunning, and there was plenty of parking space.
    Guest review by
    Fjo
    Group
  • Avg. price/night: £90.97
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 433 reviews
    A beautiful little hotel with a very clean pool and conveniently located close to Cortona and other beautiful Tuscan villages. Antonella was a very gracious host that let us enjoy the pool the day we checked out for as long as we wanted. The breakfast was one of the best we had in Italy, served by very attentive waitress and enjoyed in the company of other guest. Very reasonably priced. Will come back!
    Guest review by
    Jose
    Young couple
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 118 reviews
    We love this beautiful holiday home and the well-maintained gardens in the surroundings. The compound is conveniently located in between several historical cities and towns, and one can park right in front of his house door. Supermarkt is also close by.
    Guest review by
    Dingnan
    Group

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