A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Castellina in Chianti villas

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
7.0 out of 10, Good, (2 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is CA $249
CA $279 total
includes taxes & fees
Jul 22 - Jul 23
Villa Montecastello
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful property and great experience "
United States
edward p.
The price is CA $404
CA $637 total
includes taxes & fees
Jul 19 - Jul 20
Luxury Villa in the Florentine hills
Iron/ironing board, WiFi, bed sheets

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi

Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
Gaiole in Chianti
The price is CA $379
CA $385 total
includes taxes & fees
Jul 6 - Jul 7
Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is CA $160
CA $194 total
includes taxes & fees
Jul 4 - Jul 5
Rooster House, cooking classes and opera
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is CA $1,127
CA $1,253 total
includes taxes & fees
Aug 3 - Aug 4
Villa Marcolina
Exterior

The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is CA $284
CA $328 total
includes taxes & fees
Jul 15 - Jul 16
The three owls of san gimignano
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is CA $86
CA $407 total
includes taxes & fees
Jul 5 - Jul 6
Casa dei Renai by Rentbeat
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is CA $7,636
CA $8,445 total
includes taxes & fees
Jul 5 - Jul 6
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior detail

Exclusive Estate in Florence, Private Pool, 13 bedrooms

Exclusive Estate in Florence, Private Pool, 13 bedrooms
Oltrarno
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful stay for our large extended family. Everyone was comfortable, and the proximity to the city center was ideal. Hosts had many helpful suggestions. Make sure you ask about hiring the private chef they recommend! "
United States
Molly M.
The price is CA $9,384
CA $11,392 total
includes taxes & fees
Jul 27 - Jul 28
Exclusive Estate in Florence, Private Pool, 13 bedrooms
Exterior

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is CA $2,169
CA $2,692 total
includes taxes & fees
Jul 7 - Jul 8
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is CA $510
CA $735 total
includes taxes & fees
Jul 4 - Jul 5
Villa Il Signorino
Outdoor dining

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is CA $484
CA $647 total
includes taxes & fees
Jul 5 - Jul 6
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is CA $734
CA $807 total
includes taxes & fees
Jul 5 - Jul 6
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is CA $899
CA $988 total
includes taxes & fees
Jul 5 - Jul 6
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Exterior

Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning

Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
San Casciano in Val di Pesa
The price is CA $12,627
CA $14,147 total
includes taxes & fees
Jul 21 - Jul 22
Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
Pool

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is CA $616
CA $686 total
includes taxes & fees
Jul 4 - Jul 5
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $22,909
CA $22,909 total
includes taxes & fees
Jul 6 - Jul 7
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Terrace/patio

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is CA $4,449
CA $5,082 total
includes taxes & fees
Jul 6 - Jul 7
Golden Hour - wedding in Florence
Exterior

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Oltrarno
10.0 out of 10, Exceptional, (1 review)
"Struttura a dir poco fantastica. Siamo stati non bene benissimo e sicuramente ci ritorneremo.Approfitto anche per fare un ringraziamento a Serena e Venita per l’immensa disponibilità, professionalità e cordialità ricevuta."
United States
Giuseppe F.
The price is CA $949
CA $1,235 total
includes taxes & fees
Jul 15 - Jul 16
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Exterior

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate

My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is CA $1,237
CA $1,360 total
includes taxes & fees
Jul 5 - Jul 6
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
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 Castellina in Chianti Hotel Reviews

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"We very much enjoyed our stay here. Staff went above and beyond to accomodate us and always smiled 😁. Location was within walking distance of all the main sites to see. Breakfast was great, the spa was very nice. It was all very nice!!"
James 4-night trip
Posted less than an hour ago
IQ Hotel Firenze

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
165
Accommodation
1852 Villas
Lowest Price
CA $194
Highest Price
CA $22,909

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between CA $194 and CA $22,909 per night. These stays offer the privacy of your own space at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Castellina in Chianti?
You can choose from 1852 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad.
Why book your villa in Castellina in Chianti with Expedia?
Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad.
How can I find cheap villas in Castellina in Chianti?
The easiest way to compare cheap villas in Castellina in Chianti is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to nab awesome rates in only a few clicks.
What is there to do near my villa in Castellina in Chianti?
Whatever your interests, Castellina in Chianti has loads to keep you on the hop. Buondonno Winery, City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi are on most visitors' itineraries. Don't forget to explore Walls of Monteriggioni, Castellina Fortress and Archaeological Museum of Chianti either. With Expedia's Castellina in Chianti hotel deals, you can discover even more terrific attractions like these with the cash you save.