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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Castellina in Chianti villas

Pool

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is €5,015
includes taxes & fees
27 Feb - 28 Feb
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Terrace/patio

Viniard Villa - Residence Le Rose in Chianti

Viniard Villa - Residence Le Rose in Chianti
Castellina in Chianti
The price is €653
includes taxes & fees
2 Mar - 3 Mar
Viniard Villa - Residence Le Rose in Chianti
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is €162
includes taxes & fees
27 Feb - 28 Feb
Villa Montecastello
Exterior

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is €11,430
includes taxes & fees
27 Feb - 28 Feb
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
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
The price is €929
includes taxes & fees
15 Mar - 16 Mar
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Exterior

CountryHouse con Piscina Privata 5 min dal centro

CountryHouse con Piscina Privata 5 min dal centro
Careggi Rifredi
9.4 out of 10, Exceptional, (10 reviews)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
United States
Nancy P.
The price is €476
includes taxes & fees
2 Mar - 3 Mar
CountryHouse con Piscina Privata 5 min dal centro
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 €408
includes taxes & fees
28 Mar - 29 Mar
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is €6,215
includes taxes & fees
27 Feb - 28 Feb
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
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 €489
includes taxes & fees
28 Mar - 29 Mar
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €13,716
includes taxes & fees
27 Feb - 28 Feb
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8 reviews)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is €984
includes taxes & fees
28 Mar - 29 Mar
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is €5,072
includes taxes & fees
27 Feb - 28 Feb
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Siena
The price is €360
includes taxes & fees
27 Feb - 28 Feb
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is €872
includes taxes & fees
1 Mar - 2 Mar
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Terrace/patio

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is €3,123
includes taxes & fees
1 Mar - 2 Mar
Golden Hour - wedding in Florence
Exterior

Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is €1,319
includes taxes & fees
27 Feb - 28 Feb
Villa Capanna: A Window onto Tuscany
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)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
The price is €457
includes taxes & fees
27 Feb - 28 Feb
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Pool

Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
The price is €1,622
includes taxes & fees
2 Mar - 3 Mar
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
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 €689
includes taxes & fees
28 Mar - 29 Mar
My Exclusive Italy - Presidential Suite with view in a Luxury Wine Estate
Outdoor spa tub

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Toscana
10.0 out of 10, Exceptional, (1 review)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is €2,037
includes taxes & fees
1 Mar - 2 Mar
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
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

Hotel Boccaccio

Hotel Boccaccio

10/10 Excellent
"Great stuff. Great location. 10/10 service "
Rubiya 1-night trip
Posted 2 days ago
Hotel Boccaccio

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
27
Accommodation
1921 Villas
Lowest Price
€457
Highest Price
€6,215

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between €457 and €6,215 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 1921 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.

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