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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Castellina in Chianti villas

Exterior

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The San Leonino House
Exterior

2. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is €4,075
includes taxes & fees
23 Sept - 24 Sept
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

3. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is €863
includes taxes & fees
30 Aug - 31 Aug
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Living area

4. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
Villa Liberty in The Centre - No Ztl
Pool

5. 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 €1,017
includes taxes & fees
17 Sept - 18 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Villa, Air conditioning, Courtyard View | Exterior

6. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 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 €185
includes taxes & fees
3 Sept - 4 Sept
Villa Montecastello
Property grounds

7. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is €135
includes taxes & fees
26 Aug - 27 Aug
Rooster House, cooking classes and opera
Property grounds

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is €4,842
includes taxes & fees
26 Aug - 27 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Property grounds

9. "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)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is €1,104
includes taxes & fees
26 Aug - 27 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

10. 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 €442
includes taxes & fees
1 Sept - 2 Sept
Villa Il Signorino
Outdoor dining

11. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is €1,937
includes taxes & fees
24 Sept - 25 Sept
Villa Capanna: A Window onto Tuscany
Exterior

12. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is €1,765
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
Exterior

13. Villa "Arnilù" with Private Pool & Wi-Fi

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is €5,310
includes taxes & fees
26 Aug - 27 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

14. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
Terrace/patio

15. 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 €683
includes taxes & fees
22 Sept - 23 Sept
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

16. Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano

Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is €164
includes taxes & fees
28 Aug - 29 Aug
Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano
Outdoor dining

17. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"This was everything that it promised! The property is amazing. David was a great host and having his sister right next door was a godsend. She was very helpful with tips of places to go and ideas of how to get there. She even helped us order a taxi one morning. We had a fantastic time! It is definitely worth the visit!"
United States
Dawn L.
The price is €337
includes taxes & fees
29 Aug - 30 Aug
Luxury Villa in the Florentine hills
Outdoor dining

18. 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)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is €354
includes taxes & fees
28 Aug - 29 Aug
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Exterior

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is €13,027
includes taxes & fees
29 Aug - 30 Aug
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Outdoor dining

20. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveller
The price is €1,786
includes taxes & fees
22 Sept - 23 Sept
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
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

Palazzo Montebello

Palazzo Montebello

10/10 Excellent
"Very nice stay. Me and my wife was celebrating our 10 year anniversary with a weekend i Florence. The hotel is a 10-15 min walk from city centre, so a nice and quiet area. We stayed a total of four nights, and the room was excellent, and so was the staff. Helping us with all our requests. Will book again! Forza Viola!😊"
Jens Petter 4-night trip
Posted less than an hour ago
Palazzo Montebello

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
176
Accommodation
1785 Villas
Lowest Price
€135
Highest Price
€13,027

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between €135 and €13,027 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 1785 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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