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

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 £155
includes taxes & fees
1 Jul - 2 Jul
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 £338
includes taxes & fees
19 Jul - 20 Jul
Luxury Villa in the Florentine hills
Outdoor dining

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 £205
includes taxes & fees
30 Jun - 1 Jul
Villa 'Podere Sofia' with Mountain View, Private Terrace and Wi-Fi
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is £682
includes taxes & fees
30 Jun - 1 Jul
Villa Marcolina
Exterior

The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is £195
includes taxes & fees
15 Jul - 16 Jul
The three owls of san gimignano
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is £107
includes taxes & fees
2 Jul - 3 Jul
Rooster House, cooking classes and opera
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is £226
includes taxes & fees
19 Jul - 20 Jul
Casa dei Renai by Rentbeat
Property grounds

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 £6,116
includes taxes & fees
27 Jul - 28 Jul
Exclusive Estate in Florence, Private Pool, 13 bedrooms
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is £4,502
includes taxes & fees
30 Jun - 1 Jul
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
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 £665
includes taxes & fees
15 Jul - 16 Jul
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
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 £2,591
includes taxes & fees
30 Jun - 1 Jul
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Exterior detail

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is £2,750
includes taxes & fees
30 Jun - 1 Jul
Golden Hour - wedding in Florence
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 £430
includes taxes & fees
30 Jun - 1 Jul
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
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 £387
includes taxes & fees
30 Jun - 1 Jul
Villa Il Signorino
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is £778
includes taxes & fees
2 Jul - 3 Jul
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Exterior

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is £8,142
includes taxes & fees
30 Jun - 1 Jul
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
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 £345
includes taxes & fees
30 Jun - 1 Jul
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is £12,213
includes taxes & fees
6 Jul - 7 Jul
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

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 £365
includes taxes & fees
30 Jun - 1 Jul
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
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 £2,893
additional charges may apply
30 Jun - 1 Jul
Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
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

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

10/10 Excellent
"This is one of the most unique places I have ever stayed at. I would recommend this place and it’s location is almost perfect as well."
Kevin 3-night trip
Posted less than an hour ago
25hours Hotel Florence Piazza San Paolino

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
166
Accommodation
1806 Villas
Lowest Price
£107
Highest Price
£12,213

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between £107 and £12,213 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 1806 villas in Castellina in Chianti. No matter if you're travelling 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.