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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cortona vacation homes

A building with a stone facade, multiple windows, and a balcony.

1. 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 ￥66,819
￥74,315 total
includes taxes & fees
Oct 7 - Oct 8
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,363
￥14,609 total
includes taxes & fees
Sep 24 - Sep 25
Holiday home with panoramic terrace ideal for families and couples
A hot tub in a grassy outdoor area with a mountain view.

3. Farmhouse with mountain views hot tub

Farmhouse with mountain views hot tub
Cortona
The price is ￥38,606
￥71,567 total
includes taxes & fees
Sep 26 - Sep 27
Farmhouse with mountain views hot tub

4. 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 ￥14,238
￥17,482 total
includes taxes & fees
Oct 19 - Oct 20
Montecchio di Cortona
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 ￥8,110
￥12,075 total
includes taxes & fees
Sep 25 - Sep 26
Happy Nest Tuscany Between Florence and Rome
A stone building with a balcony, outdoor seating, and a stone staircase.

6. 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 ￥83,083
￥83,443 total
includes taxes & fees
Sep 25 - Sep 26
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

7. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥13,805
￥19,209 total
includes taxes & fees
Oct 5 - Oct 6
Dolce Casa 2 by Tiny Away
A brick building with a large sliding glass door, a brown door, and a small potted plant.

8. 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 ￥13,847
￥14,568 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

9. 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 ￥70,059
￥70,419 total
includes taxes & fees
Oct 1 - Oct 2
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A covered patio with a brick wall, a round table with chairs, and a view of greenery.

10. 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 ￥52,918
￥62,657 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Home in Villa Pandolfina near 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 ￥36,768
￥41,600 total
includes taxes & fees
Oct 2 - Oct 3
Gorgeously restored tranquil farmhouse

12. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥14,948
￥20,358 total
includes taxes & fees
Sep 24 - Sep 25
Dolce Casa 1 by Tiny Away
A stone building with a balcony, outdoor seating, and a stone staircase.

13. 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 ￥61,696
￥62,057 total
includes taxes & fees
Oct 6 - Oct 7
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

14. 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 ￥15,896
￥23,466 total
includes taxes & fees
Oct 1 - Oct 2
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A stone building with a glass table and chairs, outdoor seating, and a staircase leading to an upper level.

15. 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 ￥89,018
￥89,378 total
includes taxes & fees
Oct 1 - Oct 2
Apartment 'Pugnano Alto- Girasole' with Shared Pool, Private Terrace and Wi-Fi
A pool surrounded by lush greenery and a distant view of a town.

16. Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi

Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi
Monte San Savino
The price is ￥50,238
￥66,819 total
includes taxes & fees
Oct 21 - Oct 22
Vacation Home 'Il Granaio' with Pool, Private Terrace & Wi-Fi
A stone building with a sloped roof, a covered porch, and a small garden area.

17. Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
The price is ￥36,926
￥50,115 total
includes taxes & fees
Sep 24 - Sep 25
Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

18. Oasi del Borgo Montefollonico

Oasi del Borgo Montefollonico
Montefollonico
The price is ￥43,827
￥50,861 total
includes taxes & fees
Sep 25 - Sep 26
Oasi del Borgo Montefollonico
A narrow stone-paved alleyway with arched doorways and a wooden door.

19. Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi

Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
Scrofiano
The price is ￥65,939
￥69,597 total
includes taxes & fees
Sep 24 - Sep 25
Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
A kitchen with a tiled backsplash and three hanging utensils.

20. 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 ￥23,034
￥31,325 total
includes taxes & fees
Sep 24 - Sep 25
Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Service was top notch and Claudio at the bar made the best cocktails"
Alexander 2-night trip
Posted 17 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews
19
Accommodation
221 Vacation Homes
Lowest Price
￥12,075
Highest Price
￥89,378