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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 ￥11,218
￥14,423 total
includes taxes & fees
Oct 8 - Oct 9
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 ￥13,998
￥17,187 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥59,122
￥66,491 total
includes taxes & fees
Oct 11 - Oct 12
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A stone building with a balcony, an archway, and potted plants.

4. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is ￥22,689
￥23,398 total
includes taxes & fees
Nov 5 - Nov 6
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

5. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,973
￥11,871 total
includes taxes & fees
Oct 13 - Oct 14
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.

6. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥13,563
￥18,878 total
includes taxes & fees
Oct 13 - Oct 14
Dolce Casa 2 by Tiny Away
A brick building with a large sliding glass door, a brown door, and a small potted plant.

7. 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 ￥13,681
￥14,393 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Room

8. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥14,685
￥20,000 total
includes taxes & fees
Oct 8 - Oct 9
Dolce Casa 1 by Tiny Away
A narrow street with buildings on either side, stone walls, and a clear blue sky.

9. 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
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

10. Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is ￥23,389
￥27,996 total
includes taxes & fees
Oct 31 - Nov 1
Holiday Home 'La Casina All'angolo'
A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

11. 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 ￥19,136
￥28,704 total
includes taxes & fees
Oct 20 - Oct 21
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Room

12. Casale I Tre Cipressi

Casale I Tre Cipressi
Arezzo
Casale I Tre Cipressi
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

13. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveler
The price is ￥69,220
￥69,576 total
includes taxes & fees
Oct 8 - Oct 9
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A thatched-roof pavilion overlooking a calm lake with distant mountains.

14. 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 ￥36,539
￥41,759 total
includes taxes & fees
Oct 10 - Oct 11
Gorgeously restored tranquil farmhouse
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

15. 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 ￥15,706
￥23,185 total
includes taxes & fees
Oct 13 - Oct 14
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

16. 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 traveler
The price is ￥25,692
￥35,260 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Home in Villa Pandolfina near Montepulciano
A stone building with a balcony, outdoor seating, and a stone staircase.

17. 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 ￥90,431
￥90,785 total
includes taxes & fees
Nov 5 - Nov 6
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
A stone building with a balcony, outdoor seating, and a stone staircase.

18. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
lisciano niccone
The price is ￥60,611
￥60,965 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
A stone building with a glass table and chairs, outdoor seating, and a staircase leading to an upper level.

19. Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi

Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi
Lisciano Niccone
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Everything"
United States
Anonymous traveler
The price is ￥87,515
￥87,869 total
includes taxes & fees
Nov 5 - Nov 6
Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi
A kitchen with a granite countertop, a hanging pendant light, and a brick archway.

20. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ￥17,719
￥21,617 total
includes taxes & fees
Nov 5 - Nov 6
"Il Focolare" Superior Apartment in Monticchiello
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

Hotel Italia

Hotel Italia

10/10 Excellent
"Manuela at the front office is great. So helpful, informative and full of tips. Make sure you ask her about favorite eateries."
Fernando 1-night trip
Posted 21 hours ago
Hotel Italia

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
35
Accommodation
222 Vacation Homes
Lowest Price
￥11,871
Highest Price
￥90,785