Search Vacation Homes in Cortona

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Cortona vacation homes

Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is AED 269
AED 345 total
includes taxes & fees
7 Jun - 8 Jun
Holiday home with panoramic terrace ideal for families and couples
1 bedroom, iron/ironing board, free WiFi, bed sheets

House in the Cortona countryside

House in the Cortona countryside
Fratticciola
10.0 out of 10, Exceptional, (1 review)
"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "
United States
Nancy F.
The price is AED 392
AED 469 total
includes taxes & fees
5 Jun - 6 Jun
House in the Cortona countryside
Dining

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 AED 337
AED 435 total
includes taxes & fees
8 Jun - 9 Jun
Montecchio di Cortona
Dining

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 AED 448
AED 627 total
includes taxes & fees
28 Jun - 29 Jun
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
Property grounds

Holiday Home 'Colline' with Balcony and Wi-Fi

Holiday Home 'Colline' with Balcony and Wi-Fi
Radicofani
The price is AED 505
AED 522 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Home 'Colline' with Balcony and Wi-Fi
Iron/ironing board, WiFi, bed sheets

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 AED 460
AED 691 total
includes taxes & fees
5 Jun - 6 Jun
Double room with private bathroom in the countryside 5 minutes from Montepulciano
Exterior

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 AED 361
AED 660 total
includes taxes & fees
8 Jun - 9 Jun
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Outdoor dining

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Panicale
The price is AED 520
AED 728 total
includes taxes & fees
15 Jun - 16 Jun
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Private kitchen

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is AED 307
AED 401 total
includes taxes & fees
5 Jun - 6 Jun
Happy Nest Tuscany Between Florence and Rome
Property grounds

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Arezzo
The price is AED 328
AED 455 total
includes taxes & fees
7 Jun - 8 Jun
Dolce Casa 2 by Tiny Away
Property grounds

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 AED 414
AED 503 total
includes taxes & fees
1 Jul - 2 Jul
LANDLORD ALBACHIARA
Fridge, microwave, stovetop, dishwasher

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (9 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 AED 426
AED 520 total
includes taxes & fees
25 Jun - 26 Jun
"Il Focolare" Superior Apartment in Monticchiello
Interior

Holiday Home 'Roda' with Private Terrace, Wi-Fi and Air Conditioning

Holiday Home 'Roda' with Private Terrace, Wi-Fi and Air Conditioning
Castiglione del Lago
The price is AED 411
AED 607 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Home 'Roda' with Private Terrace, Wi-Fi and Air Conditioning
Exterior

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is AED 921
AED 1,296 total
includes taxes & fees
5 Jun - 6 Jun
Eagle House
Classic Apartment, 3 Bedrooms | Exterior

Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
The price is AED 923
AED 1,015 total
includes taxes & fees
5 Jun - 6 Jun
Rustic Holiday Home in Citta di Castello With Swimming Pool
Interior

Holiday Home 'La Casina All'angolo'

Holiday Home 'La Casina All'angolo'
Civitella in Val di Chiana
The price is AED 416
AED 527 total
includes taxes & fees
5 Jun - 6 Jun
Holiday Home 'La Casina All'angolo'
Exterior detail

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 AED 328
AED 345 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning
Terrace/patio

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is AED 961
AED 1,320 total
includes taxes & fees
7 Jun - 8 Jun
Charming Siena Countryside Stay
Pool

Agritourism in val d'orcia

Agritourism in val d'orcia
montalcino
The price is AED 640
AED 1,441 total
includes taxes & fees
7 Jun - 8 Jun
Agritourism in val d'orcia
Pool

Historic farmhouse in the Umbrian hills

Historic farmhouse in the Umbrian hills
Monte Santa Maria Tiberina
The price is AED 1,313
AED 1,714 total
includes taxes & fees
9 Jun - 10 Jun
Historic farmhouse in the Umbrian hills
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cortona Hotel Reviews

Hotel San Michele

Hotel San Michele

8/10 Good
"The location is fantastic. Just steps from the shopping and restaurants. The hotel is old fashioned and charming. The bathrooms are in need of an upgrade both fixtures and lighting. But it’s quirky ways also are the very thing that makes it charming. I would ask for a room furthest away from Via Nationale as that street can be loud at night. They have a nice breakfast each morning w an option to eat in the outdoor courtyard. Their sweet staff will bring you speciality coffees to enjoy!"
Susannah 5-night trip
Posted 2 days ago
Hotel San Michele

Explore a world of travel with Expedia