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

Villas in Castellina in Chianti

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Castellina in Chianti villas

1. The San Leonino House

The San Leonino House
Castellina in Chianti
$1,258 nightly
The price is $1,534
Sep 7 - Sep 8
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.
$1,113 nightly
The price is $1,117
Sep 17 - Sep 18
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

3. 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
$166 nightly
The price is $186
Sep 3 - Sep 4
Total with taxes and fees
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
$148 nightly
The price is $152
Sep 4 - Sep 5
Total with taxes and fees
Rooster House, cooking classes and opera
A poolside area with lounge chairs, a table with a bottle of champagne, a glass of wine, and a plate of grapes.

5. Private Tuscan Villa Estate w/ Pool & BBQ

Private Tuscan Villa Estate w/ Pool & BBQ
Poggibonsi
$2,923 nightly
The price is $3,138
Oct 3 - Oct 4
Total with taxes and fees
Private Tuscan Villa Estate w/ Pool & BBQ
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

6. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
$5,614 nightly
The price is $5,614
Sep 8 - Sep 9
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

7. "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.
$2,232 nightly
The price is $2,236
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.

8. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$516 nightly
The price is $521
Sep 3 - Sep 4
Total with taxes and fees
Villa Il Signorino
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

9. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$2,241 nightly
The price is $2,246
Sep 14 - Sep 15
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A building with a yellow exterior, a door with a number 11 sign, and a window with a potted plant.

10. The three owls of san gimignano

The three owls of san gimignano
San Gimignano
$124 nightly
The price is $126
Sep 3 - Sep 4
Total with taxes and fees
The three owls of san gimignano
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$2,042 nightly
The price is $2,047
Sep 5 - Sep 6
Total with taxes and fees
Villa Torre Among the Hills of Siena
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
$6,150 nightly
The price is $6,156
Sep 3 - Sep 4
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.

13. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

14. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"We loved this villa! David, our host, was very prompt in responding and providing additional information. The property was beautiful. We will definitely stay here again."
United States
John G.
$326 nightly
The price is $332
Sep 3 - Sep 4
Total with taxes and fees
Luxury Villa in the Florentine hills
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

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

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
$1,603 nightly
The price is $1,608
Sep 13 - Sep 14
Total with taxes and fees
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

16. 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.
$727 nightly
The price is $727
Sep 3 - Sep 4
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A two-story building with a garden, a gazebo, and a statue.

17. 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
$4,207 nightly
The price is $4,210
Oct 1 - Oct 2
Total with taxes and fees
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

18. 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
$1,324 nightly
The price is $1,329
Sep 10 - Sep 11
Total with taxes and fees
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool 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.

19. 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.
$436 nightly
The price is $436
Sep 6 - Sep 7
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$15,102 nightly
The price is $15,102
Sep 3 - Sep 4
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
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

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Beautiful historic building - lovely hotel, very charming staff. Could not have been happier at our choice of hotel! By the way, the rooftop bar is magnificent!"
Claire 1-night trip
Posted 3 hours ago
Grand Hotel Baglioni

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
171
Accommodation
1829 Villas
Lowest Price
$126
Highest Price
$15,102

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $126 and $15,102 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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