Vacation Rentals in Chianti

Vacation Rentals in Chianti

Start comparing over 6,981 rentals in Chianti and book at the best price!

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Highlights Chianti

  • Excursion to the metropolis Florence
  • Cycling tours through the unique landscape
  • Shopping and medieval fortresses in Castellina
  • Radda as a starting point for visiting the wineries

Best Vacation Rentals in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 2 Guests in Poggibonsi, Chianti
Vacation Rental for 2 Guests in Poggibonsi, Chianti, Picture 1
Vacation Rental for 2 Guests in Poggibonsi, Chianti, Picture 2
Vacation Rental for 2 Guests in Poggibonsi, Chianti, Picture 3
Vacation Rental for 2 Guests in Poggibonsi, Chianti, Picture 4
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Poggibonsi, Chianti
Vacation Rental • 484 ft² • 1 Bedroom
10.0
(4 reviews)
Small holiday home in Barberino Val d'Elsa. This is a dependence (semi-detached) with private equipped courtyard and use of the shared pool, attached from the back to the main building where the owner lives. The location is sunny and quiet and here you are in an ideal starting point to visit the most characteristic cities of Tuscany such as San Gimignano with its towers 20 km, Monteriggioni medieval town with its intact city wall 23 km and of course , the beautiful Siena 37 km with its beautiful old town and Piazza del Campo where the famous "Palio" is run twice a year. Nearby you can admir...
from $56 / night
Vacation Apartment for 2 Guests in Larciano, Pistoia Province
Vacation Apartment for 2 Guests in Larciano, Pistoia Province, Picture 1
Vacation Apartment for 2 Guests in Larciano, Pistoia Province, Picture 2
Vacation Apartment for 2 Guests in Larciano, Pistoia Province, Picture 3
Vacation Apartment for 2 Guests in Larciano, Pistoia Province, Picture 4
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Larciano, Pistoia Province
Vacation Apartment • 484 ft² • 1 Bedroom
7.0
(6 reviews)
Beautiful apartments in a complex with communal pool, consisting of a renovated farmhouse with barn, 2 km from Larciano (in the province of Pistoia). The apartments have a private entrance and outdoor area for outdoor dining. You are here in a place of great atmosphere, in hillside among olive trees and with beautiful panoramic pool. The farm offers guided tours in the farm, a small restaurant, visit to a mill and sale of oil, wine and honey from own production. Excursions: Beautiful Pistoia, with its charming Piazza Duomo with ancient bell tower, is about 17 km away. In the same square are...
from $46 / night
Vacation Apartment for 2 Guests in San Quirico D'orcia, Val D'orcia
Vacation Apartment for 2 Guests in San Quirico D'orcia, Val D'orcia, Picture 1
Vacation Apartment for 2 Guests in San Quirico D'orcia, Val D'orcia, Picture 2
Vacation Apartment for 2 Guests in San Quirico D'orcia, Val D'orcia, Picture 3
Vacation Apartment for 2 Guests in San Quirico D'orcia, Val D'orcia, Picture 4
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San Quirico D'orcia, Val D'orcia
Vacation Apartment • 377 ft² • 1 Bedroom
9.0
(4 reviews)
Vacation apartment in stone house with panoramic view near the small characteristic village of San Quirico D'Orcia (4 km). The house with the former barn, the latter attached to one side of the farmhouse, consists of three apartments: ITS604-ITS605-ITS606. The house is located on the slope of a hill with beautiful views over the typical Tuscan countryside south of Siena and is part of a family farm that produces an excellent wine. The entire property is quietly situated and has simple yet appealing furnishings. Guests have at their disposal a spacious outdoor area where you can also take yo...
from $61 / night

Prices and availability

Current Vacation rental prices Chianti

$240for 27 Apr - 4 May
$273 annual average
May
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Sep
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Apr
Average price per week

Current vacation rental availability Chianti

31%for 27 Apr - 4 May
44% annual average
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
Percentage of available rentals

Vacation rentals in Chianti

Spend your holidays in the midst of a fantastic landscape of vineyards.

The Chianti region has countless vacation rentals to offer in the midst of a breathtaking hilly landscape. Take a closer look at the apartments in the picturesque towns and cities if you want to enjoy absolute comfort with a doorman and breakfast service. You can also rent a vacation rental in Chianti, which will give you many moments of relaxation in the garden. The stone fincas often have a pool and sometimes a sauna.

Holiday in Chianti

Location and orientation

The range of hills of the same name as a perfect holiday resort to relax in

Chianti is the name of an area in Italy located in the centre of Tuscany. At the same time, Chianti is a chain of hills, the highest point of which is Monte San Michele, 893 metres high. A part of Chianti stretches over the southeastern edge of the city of Florence. Other important places are Castellina, Greve, Montefioralle and Melazzano.

Idyll in Tuscany
Idyll in Tuscany
In Chianti, the famous Chianti wine has been cultivated for centuries and its production area accounts for about one third of Tuscany as a whole.

Top 3 travel tips

1. Explore the unique landscape by bike

The main attraction of Chianti is the landscape itself. This is characterised by fertile gardens, which are also an important habitat for game. The best way to explore the region is on two wheels.

2. Visit the charming town of Castellina

Castellina is a small town where many exclusive restaurants, charming boutiques and underground shops invite you to stroll and linger. You can also visit the fortress of Palazzo Ugolino, the 12th century Castello di Fonterutoli and the 11th century Castello di Rencine not far from Villa di Rencine, which is now a winery.

3. Taste the wine of the region in Radda

A popular centre for wine lovers is Radda. Start your tour in the heart of the city, at the piazza with town hall, fountains and loggias. From here the most famous wineries of the region are very easy to reach. You will find a vineyard in the Castello di Monterinaldi, a castle of Etruscan origin.

Restaurant in Tuscany
Restaurant in Tuscany

FAQs: Vacation Rentals in Chianti

How much do you pay, on average, for vacation rentals in Chianti?

Our data shows that Chianti had an average price of $234 per night, a relatively high one for a destination in Italy.

During which months are vacation rentals cheaper in Chianti?

According to the previous year, the months that are the cheapest in Chianti are November, April and May, with average prices of $215, $221, and $221, respectively.

During which months are vacation rentals more expensive in Chianti?

Last year, the month that had the highest annual average in Chianti was January, with an average price of $258 per night. This was followed by July, with an average of $257, and then August, with $253.

Are there usually many vacation rentals available in Chianti?

When planning a vacation to Chianti, we recommend you to be proactive as 54% of rentals are usually booked, according to last year's data.

When are more vacation rentals available?

The best months to find free accommodation in Chianti are April (the average amount of properties that are free reached 64% of the total last year), May (63%), and June (57%).

When are there fewer vacation rental options available in Chianti?

The months with the lowest properties available in Chianti are, in order, August, July, and December with respective average availability figures of 20%, 37%, and 38%, based on the previous year.

How many vacation rentals does Holidu have in Chianti?

Holidu has around 17,000 vacation rentals in Chianti, provided by 92 different partners.

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