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

Holiday Homes in Cortona

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Check prices for these dates

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

Our top choices for Cortona holiday 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 NZ$163
includes taxes & fees
30 Sept - 1 Oct
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 NZ$195
includes taxes & fees
21 Oct - 22 Oct
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 NZ$755
includes taxes & fees
4 Oct - 5 Oct
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 NZ$134
includes taxes & fees
30 Sept - 1 Oct
Happy Nest Tuscany Between Florence and Rome
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

5. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is NZ$214
includes taxes & fees
1 Oct - 2 Oct
Dolce Casa 2 by Tiny Away
A brick building with a large sliding glass door, a brown door, and a small potted plant.

6. 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 NZ$162
includes taxes & fees
30 Sept - 1 Oct
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Room

7. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is NZ$226
includes taxes & fees
1 Oct - 2 Oct
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 NZ$296
includes taxes & fees
1 Oct - 2 Oct
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

9. 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 NZ$261
includes taxes & fees
5 Oct - 6 Oct
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

10. 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 NZ$321
includes taxes & fees
30 Sept - 1 Oct
Double room with private bathroom in the countryside 5 minutes from Montepulciano
A thatched-roof pavilion overlooking a calm lake with distant mountains.

11. Gorgeously restored tranquil farmhouse

Gorgeously restored tranquil farmhouse
Castiglione Del Lago PG
8.8 out of 10, Excellent, (6 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 NZ$463
includes taxes & fees
2 Oct - 3 Oct
Gorgeously restored tranquil farmhouse
A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

12. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is NZ$291
includes taxes & fees
30 Sept - 1 Oct
Holiday Home 'La Casina All'angolo'
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 NZ$5,832
includes taxes & fees
8 Oct - 9 Oct
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 NZ$349
includes taxes & fees
4 Oct - 5 Oct
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 traveller
The price is NZ$417
includes taxes & fees
5 Oct - 6 Oct
Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi
A narrow pathway leading to a building with a tree in the center, surrounded by greenery.

17. LANDLORD ALBACHIARA

LANDLORD ALBACHIARA
Ramazzano - Le Pulci
10.0 out of 10, Exceptional, (1 review)
"Ottimo appartamento, molto pulito e confortevole"
Italy
Fabio
The price is NZ$211
includes taxes & fees
30 Sept - 1 Oct
LANDLORD ALBACHIARA
Property grounds

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

Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
Anghiari
The price is NZ$221
includes taxes & fees
30 Sept - 1 Oct
Holiday Home 'Appartamento Sotto Gli Olivi' with Wi-Fi
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

19. Holiday Home in Villa Pandolfina near Montepulciano

Holiday Home in Villa Pandolfina near Montepulciano
Acquaviva
10.0 out of 10, Exceptional, (1 review)
"Pros: L'appartamento è molto spazioso e comodo con una vista panoramica sulla campagna di Montepulciano Cons: Nulla da rilevare"
Italy
Anonymous traveller
The price is NZ$697
includes taxes & fees
5 Oct - 6 Oct
Holiday Home in Villa Pandolfina near Montepulciano
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 traveller
The price is NZ$995
includes taxes & fees
30 Sept - 1 Oct
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

Villa Borgo San Pietro

Villa Borgo San Pietro

10/10 Excellent
"Well done"
PIETRO 7-night trip
Posted 21 hours ago
Villa Borgo San Pietro

Find out more about Cortona

Cortona Holiday Homes information

Number of reviews
20
Accommodation
211 Holiday Homes
Lowest Price
NZ$134
Highest Price
NZ$5,832

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