Search Vacation Homes in Chianti Region

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chianti Region vacation homes

Front of property
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Interior
Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
9.8 out of 10, Exceptional, (9)
"The house is beautiful and clean. The host is very welcoming and helpful. What more could one ask for! Thanks for having us. "
United States
Elika M.
$218 nightly
The price is $223
Jan 6 - Jan 7, 2026
Total with taxes and fees
Chianti Craft House Badia a Passignano
Fridge, oven, stovetop, dishwasher
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi

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

Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Poggibonsi
10.0 out of 10, Exceptional, (2)
"Pros: Tutto stupendo la casa la posizione è. La dolcezza della proprietaria"
Italy
Anonymous traveler
$139 nightly
The price is $143
Dec 25 - Dec 26
Total with taxes and fees
Holiday Home 'Piccolo Angolo Di Tranquillità' with Private Garden and Wi-Fi
Outdoor dining
House with views of the Chianti

House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (2)
"Great place, quaint and spacious. Beautiful view and equipped with everything needed for a pleasant stay. "
United States
Becky H.
$282 nightly
The price is $287
Dec 29 - Dec 30
Total with taxes and fees
House with views of the Chianti
Fridge, oven, stovetop, dishwasher
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

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

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveler
$187 nightly
The price is $190
Dec 30 - Dec 31
Total with taxes and fees
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Outdoor dining
Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi

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

Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi
Greve in chianti
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."
Germany
Anonymous traveler
$176 nightly
The price is $181
Jan 8 - Jan 9, 2026
Total with taxes and fees
Pet-friendly Holiday Home 'Poggio Al Mandorlo' with Garden, Whirlpool & Wi-Fi
1 bedroom, desk, WiFi, bed sheets
La Suite dei Ricordi - Apartment between Florence and Chianti

La Suite dei Ricordi - Apartment between Florence and Chianti

La Suite dei Ricordi - Apartment between Florence and Chianti
Impruneta
10.0 out of 10, Exceptional, (1)
"Carina abitazione ristrutturata tipica del centro di un paesino toscano di campagna (Impruneta a pochi chilometri da Firenze). Ottimi impianti e sistemi che rendono l'abitazione molto comoda ed attrezzata (un televisore piatto per stanza, condizionatore presente, cucina attrezzata, ecc. Parcheggi a pochi passi e gratuiti dalla sera alla mattina con negozietti a pochi passi. Massima disponibilità dei proprietari e tipica gentilezza toscana."
Italy
Anonymous traveler
$174 nightly
The price is $174
Jan 2 - Jan 3, 2026
Total with taxes and fees
La Suite dei Ricordi - Apartment between Florence and Chianti
Interior
Casa Da Vinci for two

Casa Da Vinci for two

Casa Da Vinci for two
Castiglion fibocchi
8.0 out of 10, Very Good, (1)
"Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend."
Germany
Perdita I.
$80 nightly
The price is $80
Jan 5 - Jan 6, 2026
Total with taxes and fees
Casa Da Vinci for two
Outdoor dining
Wonderful Tuscan farmhouse with large spaces and panoramic views

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, (25)
"Loved the property and views,the owner was very helpful and informative would definitely come back"
United States
Andy P.
$295 nightly
The price is $300
Dec 29 - Dec 30
Total with taxes and fees
Wonderful Tuscan farmhouse with large spaces and panoramic views
Outdoor dining
Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi

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

Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi
Rignano sull'Arno
$171 nightly
The price is $174
Jan 13 - Jan 14, 2026
Total with taxes and fees
Holiday Home 'Felciolina' with Mountain View, Private Terrace and Wi-Fi
Outdoor dining
Apartment 'Vernaccia Country House - Agriturismo' with Pool, Garden & Wi-Fi

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

Apartment 'Vernaccia Country House - Agriturismo' with Pool, Garden & Wi-Fi
BARBERINO TAVARNELLE
10.0 out of 10, Exceptional, (1)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
$337 nightly
The price is $341
Jan 3 - Jan 4, 2026
Total with taxes and fees
Apartment 'Vernaccia Country House - Agriturismo' with Pool, Garden & Wi-Fi
Pool
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
$199 nightly
The price is $201
Jan 12 - Jan 13, 2026
Total with taxes and fees
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Private Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Private Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Private Garden and Wi-Fi
Figline Valdarno
$141 nightly
The price is $145
Dec 28 - Dec 29
Total with taxes and fees
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Private Garden and Wi-Fi
2 bedrooms, free WiFi, bed sheets
Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside

Tuscan House Relax in the heart of the Tuscan countryside
Montespertoli
$137 nightly
The price is $141
Dec 28 - Dec 29
Total with taxes and fees
Tuscan House Relax in the heart of the Tuscan countryside
3 bedrooms, WiFi, bed sheets
Between Florence, Siena and Chianti

Between Florence, Siena and Chianti

Between Florence, Siena and Chianti
Montevarchi
$172 nightly
The price is $172
Dec 28 - Dec 29
Total with taxes and fees
Between Florence, Siena and Chianti
Terrace/patio
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.

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.

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.
Monteriggioni
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...
United States
Daniel D.
$402 nightly
The price is $402
Dec 26 - Dec 27
Total with taxes and fees
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.
Smart TV
House with separate entrance at the gates of Florence and Chianti

House with separate entrance at the gates of Florence and Chianti

House with separate entrance at the gates of Florence and Chianti
Impruneta
$158 nightly
The price is $166
Jan 5 - Jan 6, 2026
Total with taxes and fees
House with separate entrance at the gates of Florence and Chianti
Interior
Your nest in the Tuscany countryside

Your nest in the Tuscany countryside

Your nest in the Tuscany countryside
Certaldo - Firenze
$254 nightly
The price is $258
Jan 3 - Jan 4, 2026
Total with taxes and fees
Your nest in the Tuscany countryside
Dining
Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
$379 nightly
The price is $379
Dec 26 - Dec 27
Total with taxes and fees
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Exterior
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

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)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
$569 nightly
The price is $573
Jan 7 - Jan 8, 2026
Total with taxes and fees
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
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 Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 3 weeks ago
Hotel Borgo di Cortefreda Relais

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews
33
Accommodation
436 Vacation Homes
Lowest Price
$80
Highest Price
$573

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