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

Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Castellina in Chianti vacation homes

A stone building with multiple windows and a chimney.

1. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is CA $182
CA $206 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
A brick building with a garden, a metal fence, and a clear sky.

2. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $343
CA $429 total
includes taxes & fees
Oct 19 - Oct 20
Casa Marisa in Castellina in Chianti
A stone building with a gravel path, outdoor seating, and greenery.

3. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $381
CA $443 total
includes taxes & fees
Nov 2 - Nov 3
The Arch Among the Hills of Castellina
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

4. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (27 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is CA $128
CA $254 total
includes taxes & fees
Oct 19 - Oct 20
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A view through a wooden door of a courtyard with stone walls and potted plants.

5. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is CA $199
CA $289 total
includes taxes & fees
Oct 20 - Oct 21
Chianti Craft House Badia a Passignano
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

6. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is CA $121
CA $141 total
includes taxes & fees
Nov 5 - Nov 6
Casa Vacanze Le Case
A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

7. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $157
CA $277 total
includes taxes & fees
Oct 20 - Oct 21
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

8. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
Tavarnelle Val di Pesa
The price is CA $253
CA $374 total
includes taxes & fees
Oct 19 - Oct 20
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

9. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (11 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
The price is CA $509
CA $578 total
includes taxes & fees
Oct 29 - Oct 30
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
A rustic building with a brick facade, a small arched window, and a door.

10. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."
United States
Shanti R.
The price is CA $238
CA $296 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Tuscan-style apartment Suitable for families. Pets allowed
A swimming pool with a colorful inflatable ring and a water fountain.

11. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."
Germany
Johanna K.
The price is CA $644
CA $800 total
includes taxes & fees
Oct 19 - Oct 20
Farmhouse in Chianti
A modern kitchen with white cabinets, a wooden dining table, and a built-in oven.

12. Casa San Martino between Florence and Siena with Pool

Casa San Martino between Florence and Siena with Pool
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Wat hebben we een heerlijke tijd gehad in dit prachtige vakantiehuis in Barberino Tavarnelle! De ligging is fantastisch: rustig, sfeervol en helemaal ondergedompeld in de mooie Toscaanse omgeving. Het huis is comfortabel en van alles voorzien wat je nodig hebt voor een ontspannen verblijf. Met name de airco tijdens warme dagen was erg fijn. Een extra groot compliment voor Susanna. Ze is ontzettend gastvrij, vriendelijk en betrokken, en denkt echt met je mee. Ze was bovendien heel...
Netherlands
Anonymous traveller
The price is CA $1,211
CA $1,313 total
includes taxes & fees
Nov 2 - Nov 3
Casa San Martino between Florence and Siena with Pool
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

13. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is CA $191
CA $536 total
includes taxes & fees
Nov 15 - Nov 16
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A rustic villa with a garden, a pond, and a mountainous backdrop.

14. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is CA $13,350
CA $13,358 total
includes taxes & fees
Oct 27 - Oct 28
Ebbio – Villa and Organic Farm in Monteriggioni
An outdoor patio with a table, chairs, a grill, and a large umbrella.

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

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Tavarnelle Val di Pesa
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 $371
CA $457 total
includes taxes & fees
Oct 19 - Oct 20
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
A terrace with a table set for breakfast, a chair, and a large umbrella.

16. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (268 reviews)
"Great location with a beautiful view."
United States
Erin
The price is CA $172
CA $202 total
includes taxes & fees
Nov 18 - Nov 19
Villa La Stella - Casa per Ferie
A stone building with a sign reading "VIA DI CALZOLERIA".

17. THE TOLOMEI - apartment in the heart of the main street

THE TOLOMEI - apartment in the heart of the main street
Siena City Centre
8.4 out of 10, Very good, (5 reviews)
"I stayed for a month and found the apartment ti be very comfortable and si convenient for all that Siena has to offer."
United States
Louise B.
The price is CA $144
CA $245 total
includes taxes & fees
Oct 19 - Oct 20
THE TOLOMEI - apartment in the heart of the main street
A stone building with a courtyard, outdoor seating, and potted plants.

18. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
9.6 out of 10, Exceptional, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is CA $124
CA $474 total
includes taxes & fees
Oct 21 - Oct 22
Sorbeto Vacation Home
A dining area with a table and chairs, a sofa, and large windows with curtains.

19. '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 $1,472
CA $1,614 total
includes taxes & fees
Oct 19 - Oct 20
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Interior

20. Luce -exclusive Design Loft IN THE Heart OF Florence

Luce -exclusive Design Loft IN THE Heart OF Florence
Historic Centre of Florence
The price is CA $264
CA $309 total
includes taxes & fees
Nov 1 - Nov 2
Luce -exclusive Design Loft IN THE Heart OF 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

Bernini Palace

Bernini Palace

10/10 Excellent
"All fantastic"
Tiffany 1-night trip
Posted 4 hours ago
Bernini Palace

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Number of reviews
103
Accommodation
1882 Vacation Homes
Lowest Price
CA $141
Highest Price
CA $13,358