A hillside town with historic buildings, a church, and vineyards.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Cortona vacation homes

A park with picnic tables, a playground, and a gravel path.

1. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,241
￥14,453 total
includes taxes & fees
Oct 1 - Oct 2
Holiday home with panoramic terrace ideal for families and couples
Dining

2. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is ￥14,095
￥17,307 total
includes taxes & fees
Oct 19 - Oct 20
Montecchio di Cortona
A building with a stone facade, multiple windows, and a balcony.

3. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is ￥66,149
￥73,570 total
includes taxes & fees
Oct 11 - Oct 12
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

4. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥8,029
￥11,955 total
includes taxes & fees
Oct 2 - Oct 3
Happy Nest Tuscany Between Florence and Rome
A brick building with a large sliding glass door, a brown door, and a small potted plant.

5. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Foiano della Chiana
The price is ￥13,708
￥14,422 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

6. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥13,735
￥19,115 total
includes taxes & fees
Oct 4 - Oct 5
Dolce Casa 2 by Tiny Away
Room

7. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥14,763
￥20,116 total
includes taxes & fees
Oct 4 - Oct 5
Dolce Casa 1 by Tiny Away
A narrow street with buildings on either side, stone walls, and a clear blue sky.

8. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is ￥12,757
￥26,317 total
includes taxes & fees
Oct 1 - Oct 2
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

9. Double room with private bathroom in the countryside 5 minutes from Montepulciano

Double room with private bathroom in the countryside 5 minutes from Montepulciano
Toscana
The price is ￥19,270
￥28,905 total
includes taxes & fees
Oct 2 - Oct 3
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

10. Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
Castel Rigone
10.0 out of 10, Exceptional, (4 reviews)
"The place was amazing and as advertised! We enjoyed the area very much, the views are amazing! We shopped at the local market and enjoyed dinner in both nights we were there. If we are back in the area, we will stay here again! Saverio was very attentive and gracious. Check in and out couldn’t have been easier! "
United States
John L.
The price is ￥15,737
￥23,231 total
includes taxes & fees
Oct 5 - Oct 6
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

11. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥23,552
￥28,191 total
includes taxes & fees
Oct 31 - Nov 1
Holiday Home 'La Casina All'angolo'
A thatched-roof pavilion overlooking a calm lake with distant mountains.

12. Gorgeously restored tranquil farmhouse

Gorgeously restored tranquil farmhouse
Castiglione Del Lago PG
9.0 out of 10, Wonderful, (7 reviews)
"Jeremy is a friendly host and his farmhouse lives up to the tranquil billing! Close to the lake, Cortona and Citta della Pieve. Comfortable beds, bathrooms are fine and the kitchen is great for cooking and a nice meal"
United States
John C.
The price is ￥36,423
￥41,626 total
includes taxes & fees
Oct 3 - Oct 4
Gorgeously restored tranquil farmhouse
A stone building with a balcony, a wooden table with chairs, and a large umbrella.

13. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
Lisciano Niccone
The price is ￥516,996
￥517,353 total
includes taxes & fees
Oct 8 - Oct 9
Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria
A kitchen with a tiled backsplash and three hanging utensils.

14. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Castiglione del Lago
10.0 out of 10, Exceptional, (1 review)
"Great location in beautiful Tuscany. Very nice host and hospitallity. Would come back again!"
United States
Bin L.
The price is ￥22,803
￥31,011 total
includes taxes & fees
Oct 1 - Oct 2
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
Room

15. Casale I Tre Cipressi

Casale I Tre Cipressi
Arezzo
Casale I Tre Cipressi
A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

16. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
Monte San Savino
6.0 out of 10, (2 reviews)
"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...
Canada
Anonymous traveler
The price is ￥20,876
￥37,112 total
includes taxes & fees
Oct 4 - Oct 5
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

17. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
The price is ￥52,350
￥61,985 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Home in Villa Pandolfina near Montepulciano
Property grounds

18. Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi

Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
Anghiari
10.0 out of 10, Exceptional, (1 review)
"Comfortable and clean VRBO in the breathtakingly beautiful medieval town of Anghiari. Hosts were lovely and very kind. Location is ideal as it is only a short walk uphill to the town square with coffee shops, restaurants, and other local shops. If we ever get the privilege of visiting again, we would definitely book with these wonderful hosts!"
United States
Kaylyn C.
The price is ￥21,411
￥21,411 total
includes taxes & fees
Oct 1 - Oct 2
Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
A room with a sofa, a wooden cabinet, a table with a vase, and a chandelier.

19. Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony

Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
Monte San Savino
The price is ￥38,540
￥46,391 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Home 'Casa Corniolo' with Mountain View, Private Terrace and Balcony
A stone building with a balcony, outdoor seating, and a stone staircase.

20. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
lisciano niccone
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Alles perfect in orde."
Netherlands
Anonymous traveler
The price is ￥91,062
￥91,419 total
includes taxes & fees
Oct 3 - Oct 4
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
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

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"There is nothing to fault here, it’s a perfect hotel. Staff are brilliant, and the buildings and grounds are really well looked after. Breakfast and lunch are ideal too."
James 4-night trip
Posted 7 hours ago
Il Falconiere - Relais e Chateaux

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
21
Accommodation
221 Vacation Homes
Lowest Price
￥11,955
Highest Price
￥517,353