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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 $188
CA $214 total
includes taxes & fees
Nov 5 - Nov 6
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 $346
CA $433 total
includes taxes & fees
Oct 11 - Oct 12
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 $375
CA $438 total
includes taxes & fees
Oct 6 - Oct 7
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, (25 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 $130
CA $255 total
includes taxes & fees
Oct 6 - Oct 7
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 $200
CA $292 total
includes taxes & fees
Oct 9 - Oct 10
Chianti Craft House Badia a Passignano
A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is CA $159
CA $277 total
includes taxes & fees
Oct 7 - Oct 8
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 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 $132
CA $153 total
includes taxes & fees
Nov 2 - Nov 3
Casa Vacanze Le Case
A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

8. Your nest in the Tuscany countryside

Your nest in the Tuscany countryside
Certaldo - Firenze
The price is CA $217
CA $369 total
includes taxes & fees
Oct 11 - Oct 12
Your nest in the Tuscany countryside
A rustic building with a brick facade, a small arched window, and a door.

9. 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 $241
CA $295 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Tuscan-style apartment Suitable for families. Pets allowed
A swimming pool with a colorful inflatable ring and a water fountain.

10. 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 $650
CA $803 total
includes taxes & fees
Oct 6 - Oct 7
Farmhouse in Chianti
A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

11. 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 $513
CA $584 total
includes taxes & fees
Oct 8 - Oct 9
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
A rustic villa with a garden, a pond, and a mountainous backdrop.

12. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is CA $13,473
CA $13,481 total
includes taxes & fees
Oct 8 - Oct 9
Ebbio – Villa and Organic Farm in Monteriggioni
A modern kitchen with white cabinets, a wooden dining table, and a built-in oven.

13. 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 $1,222
CA $1,325 total
includes taxes & fees
Nov 2 - Nov 3
Casa San Martino between Florence and Siena with Pool
A garden with various plants and flowers, a pathway, and a swing set.

14. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is CA $225
CA $277 total
includes taxes & fees
Oct 6 - Oct 7
Apartment House with garden Tuscany Chianti , Florence 15km.
A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

15. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
Siena
The price is CA $116
CA $252 total
includes taxes & fees
Oct 6 - Oct 7
GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

16. 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 $321
CA $691 total
includes taxes & fees
Oct 14 - Oct 15
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
A bedroom with a bed, a nightstand, a chair, a wardrobe, and a window with curtains.

17. B&B Liveinflorence Centro Storico

B&B Liveinflorence Centro Storico
Historic Centre of Florence
9.6 out of 10, Exceptional, (11 reviews)
"Great location, excellent value for money. "
United States
Rose S.
The price is CA $241
CA $327 total
includes taxes & fees
Nov 3 - Nov 4
B&B Liveinflorence Centro Storico
An outdoor patio with a table, chairs, a grill, and a large umbrella.

18. 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 $374
CA $461 total
includes taxes & fees
Oct 6 - Oct 7
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveller
The price is CA $499
CA $586 total
includes taxes & fees
Oct 12 - Oct 13
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
A stone building with a courtyard, outdoor seating, and potted plants.

20. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
9.6 out of 10, Exceptional, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is CA $130
CA $411 total
includes taxes & fees
Oct 21 - Oct 22
Wonderful Tuscan farmhouse with large spaces and panoramic views
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Amazing hotel, amenities, food, staff & location. This was a gem to find & so enjoyable to stay at. Loved it"
Banafsheh 3-night trip
Posted 1 hour ago
Radisson Blu Hotel, Florence

Find out more about Castellina in Chianti

Castellina in Chianti Vacation Homes information

Number of reviews
185
Accommodation
1926 Vacation Homes
Lowest Price
CA $153
Highest Price
CA $13,481