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

Villas in Castellina in Chianti

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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

Exterior

1. The San Leonino House

The San Leonino House
Castellina in Chianti
$1,267 nightly
The price is $1,546
Aug 26 - Aug 27
Total with taxes and fees
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
$4,751 nightly
The price is $4,754
Sep 14 - Sep 15
Total with taxes and fees
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
$993 nightly
The price is $1,007
Aug 30 - Aug 31
Total with taxes and fees
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
TV, books

4. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
$731 nightly
The price is $731
Sep 20 - Sep 21
Total with taxes and fees
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.
$1,184 nightly
The price is $1,188
Sep 17 - Sep 18
Total with taxes and fees
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
$193 nightly
The price is $216
Aug 25 - Aug 26
Total with taxes and fees
Villa Montecastello
Property grounds

7. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
$149 nightly
The price is $153
Aug 26 - Aug 27
Total with taxes and fees
Rooster House, cooking classes and opera
Property grounds

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
$5,655 nightly
The price is $5,655
Aug 25 - Aug 26
Total with taxes and fees
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.
$1,285 nightly
The price is $1,289
Aug 26 - Aug 27
Total with taxes and fees
"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.
$526 nightly
The price is $530
Sep 1 - Sep 2
Total with taxes and fees
Villa Il Signorino
Outdoor dining

11. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$2,057 nightly
The price is $2,062
Aug 30 - Aug 31
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
Exterior

12. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$2,057 nightly
The price is $2,062
Aug 30 - Aug 31
Total with taxes and fees
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
$6,195 nightly
The price is $6,201
Aug 25 - Aug 26
Total with taxes and fees
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.
$694 nightly
The price is $694
Aug 25 - Aug 26
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Exterior

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

Cosy apartment in villa with WIFI, pool, A/C, 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.
$188 nightly
The price is $192
Aug 28 - Aug 29
Total with taxes and fees
Cosy apartment in villa with WIFI, pool, A/C, TV, terrace and panoramic view, close to San Gimig...
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.
$385 nightly
The price is $391
Aug 29 - Aug 30
Total with taxes and fees
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.
$413 nightly
The price is $413
Aug 25 - Aug 26
Total with taxes and fees
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
$15,213 nightly
The price is $15,213
Aug 25 - Aug 26
Total with taxes and fees
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 traveler
$1,334 nightly
The price is $1,339
Aug 30 - Aug 31
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"Very comfortable stay. Clean and kids friendly."
Nga Kam 2-night trip
Posted less than an hour ago
IQ Hotel Firenze

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
176
Accommodation
1829 Villas
Lowest Price
$153
Highest Price
$15,213

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $153 and $15,213 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.

Explore a world of travel with Expedia