Vacation Rentals in Chianti

Vacation Rentals in Chianti

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

Find Vacation Rentals in Chianti

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
more...
Poggibonsi, Chianti
Vacation Rental • 323 ft² • 1 Bedroom
9.0
(23 reviews)
Farm complex consisting of a farmhouse, originally a 15th century lookout tower, a small 18th century church, a former barn (ITC829) and two independent rural buildings (ITC907+ 525). Besides the owner's house, in the main part there are also two beautiful semi-detached houses (ITC952 and ITC243); the barn is independent. The property has undergone an attentive and careful renovation, the furnishings are of optimal level, specially designed with a linear and bright design. Each accommodation unit has satellite TV and private equipped outdoor areas. Access to the house via gravel road 1 km l...
from $59 / night
Vacation Rental for 2 Guests in Loro Ciuffenna, Chianti
Vacation Rental for 2 Guests in Loro Ciuffenna, Chianti, Picture 1
Vacation Rental for 2 Guests in Loro Ciuffenna, Chianti, Picture 2
Vacation Rental for 2 Guests in Loro Ciuffenna, Chianti, Picture 3
Vacation Rental for 2 Guests in Loro Ciuffenna, Chianti, Picture 4
more...
Loro Ciuffenna, Chianti
Vacation Rental • 377 ft² • 1 Bedroom
8.9
(17 reviews)
This wonderful farmhouse with a bedroom is situated in Tuscany. It has one bedroom and can accommodate 2 guests. It is suitable for a couple on a romantic holiday, it offers a shared swimming pool ideal for relaxing hours.During your stay here, you can easily reach Gambassi Terme, Montignoso, Volterra, Siena, and Certaldo. While restaurants are 1.5 km away from the farmhouse, supermarkets can be found 3 km away.Here, you will find a living room where you can enjoy a TV in front of the fireplace. There is an open-plan kitchenette to cherish home-cooked food. This farmhouse is centrally heate...
from $86 / 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
more...
San Quirico D'orcia, Val D'orcia
Vacation Apartment • 377 ft² • 1 Bedroom
9.0
(8 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

$271for 22 Jun - 29 Jun
$275 annual average
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Average price per week

Current vacation rental availability Chianti

26%for 22 Jun - 29 Jun
42% annual average
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
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.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

500+ more