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

Castellina in Chianti Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Castellina in Chianti vacation homes

Property grounds

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"Very quiet and nice place to stay. Host’s were great and easy to communicate with"
United States
Tanya G.
The price is CA $225
CA $253 total
includes taxes & fees
Jul 24 - Jul 25
Villa with large garden in the Chianti hills
TV

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $372
CA $459 total
includes taxes & fees
Jul 22 - Jul 23
Casa Marisa in Castellina in Chianti
Outdoor dining

The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $398
CA $461 total
includes taxes & fees
Aug 2 - Aug 3
The Arch Among the Hills of Castellina
Interior

Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Barberino Tavarnelle
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $225
CA $319 total
includes taxes & fees
Jul 28 - Jul 29
Chianti Craft House Badia a Passignano
Interior

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is CA $880
CA $1,024 total
includes taxes & fees
Jul 21 - Jul 22
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Pool

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
"Pros: Posto meraviglioso. Bellissima location e bellissimo panorama Cons: Un po' più di cura e pulizia nella zona piscina. Jacuzzi chiusa e pensavamo di trovarla aperta"
Italy
Anonymous traveller
The price is CA $898
CA $1,065 total
includes taxes & fees
Aug 14 - Aug 15
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Outdoor dining

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Colle Val d'Elsa
10.0 out of 10, Exceptional, (2 reviews)
"Schöne Zimmer, Dusche sehr modern und sehr sauber, Fernseher mit Internet-Anschluss sehr gut"
Germany
Rupert H.
The price is CA $634
CA $705 total
includes taxes & fees
Jul 22 - Jul 23
Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi
Outdoor dining

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
BARBERINO TAVARNELLE
10.0 out of 10, Exceptional, (1 review)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
The price is CA $499
CA $586 total
includes taxes & fees
Jul 26 - Jul 27
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Living area

Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse

Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse
Greve in Chianti
The price is CA $513
CA $593 total
includes taxes & fees
Aug 15 - Aug 16
Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse
Interior

THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is CA $192
CA $244 total
includes taxes & fees
Jul 21 - Jul 22
THE CASINA OF SANT 'AGOSTINO
Spa

Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $144
CA $265 total
includes taxes & fees
Jul 21 - Jul 22
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Pool

Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi

Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Rosennano
The price is CA $523
CA $529 total
includes taxes & fees
Jul 25 - Jul 26
Apartment Casale Rosennano - Riserva with Shared Garden & Wi-Fi
Exterior

'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi

'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi
San Gimignano
The price is CA $1,323
CA $1,328 total
includes taxes & fees
Aug 2 - Aug 3
'La Ripa - Apartment I Ghiri' with Shared Pool & Wi-Fi
Exterior

Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is CA $5,133
CA $5,133 total
includes taxes & fees
Aug 16 - Aug 17
Ebbio – Villa and Organic Farm in Monteriggioni
Outdoor pool

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is CA $178
CA $203 total
includes taxes & fees
Aug 2 - Aug 3
Casa Vacanze Le Case
Exterior

Vana Hills House - Three Bedroom House, Sleeps 8

Vana Hills House - Three Bedroom House, Sleeps 8
Monteriggioni
The price is CA $194
CA $434 total
includes taxes & fees
Aug 8 - Aug 9
Vana Hills House - Three Bedroom House, Sleeps 8
Outdoor dining

Apartment 'Volpe' with Private Pool, Wi-Fi and Air Conditioning

Apartment 'Volpe' with Private Pool, Wi-Fi and Air Conditioning
San Gimignano
The price is CA $1,078
CA $1,214 total
includes taxes & fees
Aug 9 - Aug 10
Apartment 'Volpe' with Private Pool, Wi-Fi and Air Conditioning
Pool

Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
San Gimignano
The price is CA $772
CA $780 total
includes taxes & fees
Jul 22 - Jul 23
Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
Property grounds

Frem SGV between Chianti Florence and Arezzo

Frem SGV between Chianti Florence and Arezzo
San Giovanni Valdarno
10.0 out of 10, Exceptional, (13 reviews)
"The property is of new and modern construction with all the amenities you would want. The grounds are landscaped, with beautiful trees and plants and the front deck is perfect for evening wine and snacks overlooking countryside hills in the distance. We would definitely stay here again while visiting this region of Tuscany. Centrally located to be able to reach northern and southern Tuscany by car or train."
United States
John K.
The price is CA $184
CA $273 total
includes taxes & fees
Jul 23 - Jul 24
Frem SGV between Chianti Florence and Arezzo
Outdoor spa tub

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
San Gimignano
9.2 out of 10, Wonderful, (13 reviews)
"Great place in the Tuscany area. The views are spectacular, the property is just like the pictures. Would definitely stay here again"
United States
Valerie S.
The price is CA $1,078
CA $1,190 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Il Malaspina

Il Malaspina

10/10 Excellent
"Fabulous stay at the Malaspina! Beautiful hotel! Divine scents & gorgeous luxurious toiletries! Fantastic breakfast! Convenient location to all the sites and central historic Florence. Amazingly appointed room! Just didn’t realize that the bottled water in the room was complimentary & hence did not touch! 﫣 Some minor issues with the climate control in the room but staff did their utmost to resolve the problems. Wouldn’t hesitate to return to the Il Malaspina when we return to Florence. A truly memorable stay! Thank you….beautiful Firenze….magical memories made! ❤️🙏"
Hannah 3-night trip
Posted 4 hours ago
Il Malaspina

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Number of reviews
133
Accommodation
1762 Vacation Homes
Lowest Price
CA $203
Highest Price
CA $5,133