A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Search Vacation Homes in Chianti Region

  • 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
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chianti Region vacation homes

Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is AED 592
AED 840 total
includes taxes & fees
22 Jul - 23 Jul
Chianti Craft House Badia a Passignano
Living area

casagreve - stylish house in Tuscan village - breathtaking view from its terrace

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (10 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
The price is AED 1,345
AED 1,525 total
includes taxes & fees
15 Aug - 16 Aug
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Property grounds

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"Very quiet and nice place to stay. Host’s were great and easy to communicate with"
United States
Tanya G.
The price is AED 672
AED 765 total
includes taxes & fees
23 Jul - 24 Jul
Villa with large garden in the Chianti hills
Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is AED 2,306
AED 2,681 total
includes taxes & fees
20 Jul - 21 Jul
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Property grounds

Frem SGV between Chianti Florence and Arezzo

Frem SGV between Chianti Florence and Arezzo
San Giovanni Valdarno
10.0 out of 10, Exceptional, (13 reviews)
"The property is of new and modern construction with all the amenities you would want. The grounds are landscaped, with beautiful trees and plants and the front deck is perfect for evening wine and snacks overlooking countryside hills in the distance. We would definitely stay here again while visiting this region of Tuscany. Centrally located to be able to reach northern and southern Tuscany by car or train."
United States
John K.
Frem SGV between Chianti Florence and Arezzo
TV

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 976
AED 1,202 total
includes taxes & fees
21 Jul - 22 Jul
Casa Marisa in Castellina in Chianti
Outdoor dining

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
BARBERINO TAVARNELLE
10.0 out of 10, Exceptional, (1 review)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
The price is AED 1,961
AED 2,188 total
includes taxes & fees
26 Jul - 27 Jul
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Pool

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is AED 1,134
AED 1,403 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Outdoor dining

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Colle Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"Schöne Zimmer, Dusche sehr modern und sehr sauber, Fernseher mit Internet-Anschluss sehr gut"
Germany
Rupert H.
The price is AED 1,660
AED 1,848 total
includes taxes & fees
21 Jul - 22 Jul
Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Coffee/tea maker, fridge, microwave, oven

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Vaggio
The price is AED 2,647
AED 2,660 total
includes taxes & fees
21 Jul - 22 Jul
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Pool

Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Rosennano
The price is AED 1,508
AED 1,525 total
includes taxes & fees
20 Jul - 21 Jul
Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Outdoor dining

Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
9.6 out of 10, Exceptional, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is AED 437
AED 1,172 total
includes taxes & fees
20 Jul - 21 Jul
Wonderful Tuscan farmhouse with large spaces and panoramic views
Outdoor dining

The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 1,043
AED 1,207 total
includes taxes & fees
2 Aug - 3 Aug
The Arch Among the Hills of Castellina
Outdoor dining

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is AED 412
AED 1,092 total
includes taxes & fees
12 Aug - 13 Aug
House with views of the Chianti
Pool

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful stay in a wonderful Italian villa. "
United States
Jessica C.
The price is AED 1,777
AED 1,786 total
includes taxes & fees
7 Aug - 8 Aug
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Pool

MIchelangelo Apartment with garden

MIchelangelo Apartment with garden
San Gersolé-torre Rosse
8.0 out of 10, Very Good, (1 review)
"The adjourned apartments to make one large apartment are very nice, clean, nicely decorated and in a nice quiet location. The city of Florence is only a short car journey away, 15 minutes maximum and car parking is easy to find. The only downside was a lack of wine glasses, there was none. However other small glassware was available. Would I stay ehre again, that is a yes as the apartments were very clean and included air-conditioning and little extras such as soap, shower gel etc."
United States
Andrew B.
The price is AED 2,063
AED 2,958 total
includes taxes & fees
31 Jul - 1 Aug
MIchelangelo Apartment with garden
Outdoor spa tub

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
San Gimignano
9.2 out of 10, Wonderful, (13 reviews)
"Great place in the Tuscany area. The views are spectacular, the property is just like the pictures. Would definitely stay here again"
United States
Valerie S.
The price is AED 2,823
AED 3,118 total
includes taxes & fees
16 Aug - 17 Aug
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
Dining

Masaccio Apartment with garden

Masaccio Apartment with garden
Impruneta
The price is AED 2,292
AED 3,210 total
includes taxes & fees
3 Aug - 4 Aug
Masaccio Apartment with garden
Outdoor dining

Raffaello Apartment with garden

Raffaello Apartment with garden
San Gersolé-torre Rosse
The price is AED 1,375
AED 2,202 total
includes taxes & fees
11 Aug - 12 Aug
Raffaello Apartment with garden
Dining

Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is AED 756
AED 1,176 total
includes taxes & fees
26 Jul - 27 Jul
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
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 Chianti Region Hotel Reviews

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town

8/10 Good
"it was pleasant and clean"
Natasha 4-night trip
Posted 22 hours ago
hu Firenze Certosa camping in town

Explore a world of travel with Expedia