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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chianti Region vacation homes

A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

1. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is ￥19,932
￥22,629 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

2. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is ￥14,208
￥28,284 total
includes taxes & fees
Nov 2 - Nov 3
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
An outdoor patio with a table, chairs, and a view of a landscape.

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

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is ￥19,002
￥25,512 total
includes taxes & fees
Nov 2 - Nov 3
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
A view through a wooden door of a courtyard with stone walls and potted plants.

4. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (13 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is ￥21,993
￥31,846 total
includes taxes & fees
Nov 1 - Nov 2
Chianti Craft House Badia a Passignano
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

5. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is ￥21,113
￥59,293 total
includes taxes & fees
Nov 15 - Nov 16
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A garden with a lawn, three white lounge chairs, and a pergola.

6. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is ￥21,113
￥27,623 total
includes taxes & fees
Nov 2 - Nov 3
Apartment House with garden Tuscany Chianti , Florence 15km.
A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

7. A cozy little house

A cozy little house
Loro Ciuffenna
The price is ￥12,316
￥15,483 total
includes taxes & fees
Nov 4 - Nov 5
A cozy little house
A brick building with a garden, a metal fence, and a clear sky.

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is ￥38,004
￥47,505 total
includes taxes & fees
Nov 1 - Nov 2
Casa Marisa in Castellina in Chianti
A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is ￥9,818
￥19,319 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
An outdoor patio with a table, chairs, a grill, and a large umbrella.

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

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Tavarnelle Val di Pesa
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 ￥42,116
￥51,645 total
includes taxes & fees
Nov 16 - Nov 17
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

11. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
Tavarnelle Val di Pesa
The price is ￥31,353
￥45,077 total
includes taxes & fees
Nov 1 - Nov 2
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
An outdoor terrace with a table and chairs, overlooking a town square with buildings and a statue.

12. 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, (11 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 ￥56,465
￥63,700 total
includes taxes & fees
Nov 6 - Nov 7
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
A stone building with a gravel path, outdoor seating, and greenery.

13. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is ￥38,004
￥44,866 total
includes taxes & fees
Nov 2 - Nov 3
The Arch Among the Hills of Castellina
A rustic interior with a stone fireplace, wooden beams, a sofa, and a staircase leading to a door.

14. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence
Rignano sull'Arno
8.0 out of 10, Very good, (1 review)
"Pros: Alles was goed voorbereid en ruim aanwezig. Keuken/kook benodigdheden, shampoos, fles wijn, fruitmandje met bananen en appels. Pro-actief en vriendelijk optreden van de host; zo werd verwarming aangezet bij minder goed weer. Cons: Niet van toepassing. We hebben een hele fijne week gehad."
Netherlands
Anonymous traveler
The price is ￥32,022
￥32,726 total
includes taxes & fees
Nov 27 - Nov 28
Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence
A stone building with a tiled roof, a small window, and a door.

15. Mhateria Relais

Mhateria Relais
Rignano Sull' Arno
10.0 out of 10, Exceptional, (1 review)
"Eine tolle Immobilie, die tatsächlich so gut wie sie beschrieben ist, auch ist."
Germany
Thomas K.
The price is ￥39,588
￥48,649 total
includes taxes & fees
Nov 2 - Nov 3
Mhateria Relais
A living room with a TV, a sofa, and a dining area with chairs.

16. House with a separate entrance on the outskirts of Florence and Chianti

House with a separate entrance on the outskirts of Florence and Chianti
Impruneta
The price is ￥15,881
￥28,585 total
includes taxes & fees
Nov 2 - Nov 3
House with a separate entrance on the outskirts of Florence and Chianti
A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

17. 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 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveler
The price is ￥34,374
￥34,902 total
includes taxes & fees
Nov 1 - Nov 2
Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
An aerial view of a traditional villa with multiple buildings, surrounded by lush greenery and trees.

18. Nice apartment for 6 people with A/C, WIFI, pool, TV, balcony and pets allowed, close to Florence

Nice apartment for 6 people with A/C, WIFI, pool, TV, balcony and pets allowed, close to Florence
Impruneta
The price is ￥23,373
￥31,115 total
includes taxes & fees
Nov 1 - Nov 2
Nice apartment for 6 people with A/C, WIFI, pool, TV, balcony and pets allowed, close to Florence
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

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

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A stone building with a covered outdoor seating area and a brick pathway.

20. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (1 review)
"We stayed for a week at La Ripa. It is a very beautiful and quiet place. It is a few minutes from San Gimignano and it is a central place to visit nice villages in Toscany. Rodrigo was there to welcome us and securing for us an optimal stay. He was amicable and available. This is a place we are highly recommending."
Canada
Anne-Marie M.
The price is ￥85,279
￥85,808 total
includes taxes & fees
Nov 1 - Nov 2
Apartment 'La Ripa - Master' with Shared Pool 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

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"The property is amazing and the wine is even better. The only thing is I wish the lunch and dinner menus weee different"
Owen 1-night trip
Posted 12 hours ago
Castello Vicchiomaggio

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews
225
Accommodation
447 Vacation Homes
Lowest Price
￥15,483
Highest Price
￥85,808

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