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

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 AED 466
AED 529 total
includes taxes & fees
8 Nov - 9 Nov
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 AED 332
AED 661 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 442
AED 594 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 512
AED 741 total
includes taxes & fees
11 Nov - 12 Nov
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 AED 492
AED 1,368 total
includes taxes & fees
21 Nov - 22 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A garden with various plants and flowers, a pathway, and a swing set.

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 AED 493
AED 645 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 288
AED 362 total
includes taxes & fees
6 Nov - 7 Nov
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 AED 888
AED 1,110 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 229
AED 451 total
includes taxes & fees
5 Nov - 6 Nov
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 AED 929
AED 1,150 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 730
AED 1,049 total
includes taxes & fees
1 Nov - 2 Nov
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

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 AED 1,311
AED 1,491 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 888
AED 1,048 total
includes taxes & fees
2 Nov - 3 Nov
The Arch Among the Hills of Castellina
A wooden table with two wine glasses and a bottle of wine, set outdoors with a view of greenery and hills.

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 AED 748
AED 765 total
includes taxes & fees
27 Nov - 28 Nov
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 AED 922
AED 1,133 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 369
AED 664 total
includes taxes & fees
2 Nov - 3 Nov
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 AED 800
AED 813 total
includes taxes & fees
1 Nov - 2 Nov
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 AED 544
AED 724 total
includes taxes & fees
1 Nov - 2 Nov
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
The price is AED 1,135
AED 1,144 total
includes taxes & fees
31 Oct - 1 Nov
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 AED 1,987
AED 1,999 total
includes taxes & fees
1 Nov - 2 Nov
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 21 hours ago
Castello Vicchiomaggio

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