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

Villas in Castellina in Chianti

Check prices for these dates

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

Our top choices for Castellina in Chianti villas

1. The San Leonino House

The San Leonino House
Castellina in Chianti
$1,257 nightly
The price is $1,533
Aug 31 - Sep 1
Total with taxes and fees
The San Leonino House
A stone building with a swimming pool, wooden deck, and a tall tree.

2. 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.
$1,112 nightly
The price is $1,117
Sep 18 - Sep 19
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
$148 nightly
The price is $152
Sep 1 - Sep 2
Total with taxes and fees
Rooster House, cooking classes and opera
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

4. 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
$190 nightly
The price is $213
Sep 6 - Sep 7
Total with taxes and fees
Villa Montecastello
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

5. "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)
$2,230 nightly
The price is $2,235
Sep 18 - Sep 19
Total with taxes and fees
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

6. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$522 nightly
The price is $527
Sep 5 - Sep 6
Total with taxes and fees
Villa Il Signorino
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
$5,610 nightly
The price is $5,610
Aug 30 - Aug 31
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$2,041 nightly
The price is $2,045
Aug 30 - Aug 31
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$2,041 nightly
The price is $2,045
Aug 30 - Aug 31
Total with taxes and fees
Villa Torre Among the Hills of Siena
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

10. 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.
$330 nightly
The price is $336
Aug 30 - Aug 31
Total with taxes and fees
Luxury Villa in the Florentine hills
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
$6,146 nightly
The price is $6,151
Sep 2 - Sep 3
Total with taxes and fees
Villa "Arnilù" with Private Pool & Wi-Fi
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

12. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A stone building with a sloped roof, arched windows, and a small garden with flowers and shrubs.

13. Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...

Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
Nice apartment in villa with A/C, pool, WIFI, TV, terrace and panoramic view, close to San Gimig...

14. 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
$4,543 nightly
The price is $4,547
Sep 29 - Sep 30
Total with taxes and fees
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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.
$692 nightly
The price is $692
Aug 30 - Aug 31
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

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

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
$1,602 nightly
The price is $1,607
Sep 16 - Sep 17
Total with taxes and fees
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

17. 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.
$409 nightly
The price is $409
Aug 30 - Aug 31
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

18. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very Good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

19. 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 traveler
$1,323 nightly
The price is $1,328
Aug 30 - Aug 31
Total with taxes and fees
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
A building with a large entrance, potted plants, and a statue in the foreground.

20. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
$2,517 nightly
The price is $2,520
Sep 1 - Sep 2
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & 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

Starhotels Tuscany

Starhotels Tuscany

10/10 Excellent
"Great location to be close to the airport but also get into the city center of Florence. Tram stop is in front of hotel so very easy to get luggage to airport for 2 euros/adult. Restaurant was great and very accommodating for kids. Room was clean and spacious."
Augustus 1-night trip
Posted 20 hours ago
Starhotels Tuscany

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
178
Accommodation
1829 Villas
Lowest Price
$152
Highest Price
$6,151

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $152 and $6,151 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 1829 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.
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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