Holiday Homes in Chianti Region

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Chianti Region

Our top choices for Chianti Region holiday homes

Casa Riccimballa

8.0 out of 10, Very good, (1)
"Lugar tranquilo, reservamos para 7 personas y lo que nos decepciono fue encontrar que solo tenía una regadera para todas las recámaras..."
The price is AU$2,221
includes taxes & fees
28 Aug - 29 Aug
Casa Riccimballa

Borgo Argiano

10.0 out of 10, Exceptional, (68)
"Very comfortable stay. "
The price is AU$1,081
includes taxes & fees
31 Aug - 1 Sept
Borgo Argiano

Villa with large garden in the Chianti hills

9.4 out of 10, Exceptional, (70)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
The price is AU$215
includes taxes & fees
15 Sept - 16 Sept
Villa with large garden in the Chianti hills

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
The price is AU$223
includes taxes & fees
29 Aug - 30 Aug
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

country house with garden ,pool,children's play area ,Tuscany,15 from Florence

9.8 out of 10, Exceptional, (80)
"The place was everything we wanted and more. The perfect size house, beautiful grounds and pool, and I can’t imagine a better town (San Casciano) to be based out of. Sonia was the most wonderful host, giving us amazing information about the town and things to do in the area that we would have not found otherwise. We can’t recommend this place more highly!!!!"
The price is AU$381
includes taxes & fees
1 Sept - 2 Sept
country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

10.0 out of 10, Exceptional, (1)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
The price is AU$290
includes taxes & fees
27 Aug - 28 Aug
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Casale Beatrice located in the wonderful Tuscan countryside

8.0 out of 10, Very good, (1)
"Nice house with huge and pleasant garden located in a magnificient area close to Firenze, Pisa, San Giminiano, Lucca... "
The price is AU$323
includes taxes & fees
2 Sept - 3 Sept
Casale Beatrice located in the wonderful Tuscan countryside

A LUXURY VILLA ON THE HILLS OF FLORENCE

The price is AU$19,578
includes taxes & fees
31 Aug - 1 Sept
A LUXURY VILLA ON THE HILLS OF FLORENCE

Room 'Countryhometuscany - Courtyard' with Shared Pool, Private Terrace and Wi-Fi

The price is AU$502
includes taxes & fees
20 Sept - 21 Sept
Room 'Countryhometuscany - Courtyard' with Shared Pool, Private Terrace and Wi-Fi

Wonderful Tuscan farmhouse with large spaces and panoramic views

9.8 out of 10, Exceptional, (21)
"If you are looking for a beautiful area close to but not in Florence this is the place for you! Rustic Tuscan farmhouse that is just lovely with beautiful views. Mattia is a wonderful host with great recommendations for visits and food. This is close to all that Tuscany has to offer, would definitely stay here again ."
The price is AU$470
includes taxes & fees
27 Aug - 28 Aug
Wonderful Tuscan farmhouse with large spaces and panoramic views

Between Florence, Siena and Chianti

The price is AU$262
includes taxes & fees
2 Sept - 3 Sept
Between Florence, Siena and Chianti

THE CASTELLETTO

The price is AU$305
includes taxes & fees
27 Aug - 28 Aug
THE CASTELLETTO

Vacation Home "Casalino" with Shared Pool, Shared Garden & Wi-Fi

The price is AU$1,668
includes taxes & fees
9 Sept - 10 Sept
Vacation Home "Casalino" with Shared Pool, Shared Garden & Wi-Fi

Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
The price is AU$667
includes taxes & fees
27 Aug - 28 Aug
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.

Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi

9.4 out of 10, Exceptional, (3)
"Cons: Das direkt neben an 2 Hunde den ganzen Tag im Garten waren,die nicht kompatibel waren.Unsere Hunde mussten dann drinnen oder an die Leine. Das hat unseren Urlaub sehr stressig gemacht,und wir hätten es nicht gebucht wenn wir das gewusst hätten.Spühlmaschine schon länger kaputt. Etwas mehr Geschirr wär schön."
The price is AU$398
includes taxes & fees
6 Sept - 7 Sept
Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi

Your nest in the Tuscany countryside

The price is AU$368
includes taxes & fees
17 Sept - 18 Sept
Your nest in the Tuscany countryside

Chianti Craft House Badia a Passignano

9.8 out of 10, Exceptional, (7)
"Great food in the area. Beautiful church tour and a fantastic host for our stay!"
The price is AU$378
includes taxes & fees
6 Sept - 7 Sept
Chianti Craft House Badia a Passignano

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

The price is AU$429
includes taxes & fees
27 Aug - 28 Aug
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi

The price is AU$277
includes taxes & fees
13 Sept - 14 Sept
Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi

Tuscan House Relax in the heart of the Tuscan countryside

The price is AU$202
includes taxes & fees
27 Aug - 28 Aug
Tuscan House Relax in the heart of the Tuscan countryside
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chianti Region Hotel Reviews

Find out more about Chianti Region

Find out more about Chianti Region

Chianti Region Holiday Homes information

Number of reviews
208
Accommodation
433 Holiday Homes
Lowest Price
AU$215
Highest Price
AU$1,162

Explore a world of travel with Expedia

Explore a world of travel with Expedia