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
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Castellina in Chianti villas

Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is SAR 425
SAR 516 total
includes taxes & fees
24 Jul - 25 Jul
Rooster House, cooking classes and opera
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 SAR 669
SAR 748 total
includes taxes & fees
21 Jul - 22 Jul
Villa Montecastello
Exterior

Romantic stylish villa with private pool & splendid view

Romantic stylish villa with private pool & splendid view
Panzano In Chianti
9.8 out of 10, Exceptional, (24 reviews)
"Beautiful location with spectacular views."
United States
lawrence s.
Romantic stylish villa with private pool & splendid view
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is SAR 3,058
SAR 3,398 total
includes taxes & fees
21 Jul - 22 Jul
Villa Marcolina
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, (9 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is SAR 3,093
SAR 3,196 total
includes taxes & fees
24 Jul - 25 Jul
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Pool

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is SAR 6,706
SAR 8,772 total
includes taxes & fees
20 Aug - 21 Aug
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is SAR 18,655
SAR 20,803 total
includes taxes & fees
21 Jul - 22 Jul
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
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 SAR 1,353
SAR 1,890 total
includes taxes & fees
22 Jul - 23 Jul
Villa Il Signorino
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 SAR 12,071
SAR 16,106 total
includes taxes & fees
28 Jul - 29 Jul
Villa 'Il Conventino' with Private Pool, Wi-Fi, and Air Conditioning
Pool

Podere Le Casette - Five Bedroom Villa, Sleeps 10

Podere Le Casette - Five Bedroom Villa, Sleeps 10
Cassia
10.0 out of 10, Exceptional, (1 review)
"The home was recently renovated immaculately and is an incredible place to enjoy Tuscany as well as Florence. The pictures don’t do it justice. We enjoyed our stay and would recommend to any group of any age. The views will last forever."
United States
Geoff B.
The price is SAR 3,207
SAR 5,050 total
includes taxes & fees
16 Aug - 17 Aug
Podere Le Casette - Five Bedroom Villa, Sleeps 10
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is SAR 6,635
SAR 7,584 total
includes taxes & fees
26 Jul - 27 Jul
Villa Torre Among the Hills of Siena
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is SAR 228
SAR 1,082 total
includes taxes & fees
21 Jul - 22 Jul
Casa dei Renai by Rentbeat
Property grounds

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is SAR 4,593
SAR 5,543 total
includes taxes & fees
26 Jul - 27 Jul
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
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 SAR 1,074
SAR 1,671 total
includes taxes & fees
26 Jul - 27 Jul
Luxury Villa in the Florentine hills
Exterior

Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is SAR 21,218
SAR 22,811 total
includes taxes & fees
21 Jul - 22 Jul
Villa "Arnilù" with Private Pool & Wi-Fi
Exterior

The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is SAR 576
SAR 666 total
includes taxes & fees
24 Jul - 25 Jul
The three owls of san gimignano
Outdoor dining

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is SAR 7,214
SAR 7,231 total
includes taxes & fees
23 Jul - 24 Jul
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Pool

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is SAR 40,416
SAR 42,491 total
includes taxes & fees
13 Aug - 14 Aug
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Terrace/patio

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is SAR 2,169
SAR 2,693 total
includes taxes & fees
21 Jul - 22 Jul
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
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

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"The rooftop pool was amazing. The breakfast buffet was awesome."
April 1-night trip
Posted 2 hours ago
The Social Hub Florence Belfiore

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between SAR 516 and SAR 42,491 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 1912 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.

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