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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Castellina in Chianti villas

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

1. 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
$158 nightly
The price is $177
Sep 28 - Sep 29
Total with taxes and fees
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
$146 nightly
The price is $149
Sep 29 - Sep 30
Total with taxes and fees
Rooster House, cooking classes and opera
A stone building with a swimming pool, wooden deck, and a tall tree.

3. 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.
$2,043 nightly
The price is $2,048
Oct 4 - Oct 5
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

4. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub 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.
$1,663 nightly
The price is $1,668
Oct 6 - Oct 7
Total with taxes and fees
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub 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.

5. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$478 nightly
The price is $483
Sep 28 - Sep 29
Total with taxes and fees
Villa Il Signorino
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

6. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
$6,288 nightly
The price is $6,291
Oct 12 - Oct 13
Total with taxes and fees
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
$7,989 nightly
The price is $7,989
Sep 28 - Sep 29
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A villa with a swimming pool, surrounded by lush greenery and vineyards.

8. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
$6,834 nightly
The price is $6,839
Oct 14 - Oct 15
Total with taxes and fees
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
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
$1,947 nightly
The price is $1,951
Oct 17 - Oct 18
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

10. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,947 nightly
The price is $1,951
Oct 17 - Oct 18
Total with taxes and fees
Villa Torre Among the Hills of Siena
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

11. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
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
$6,043 nightly
The price is $6,048
Sep 28 - Sep 29
Total with taxes and fees
Villa "Arnilù" with Private Pool & Wi-Fi
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

13. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
$2,924 nightly
The price is $2,924
Oct 18 - Oct 19
Total with taxes and fees
Villa Mami: A Tuscan Retreat of Elegance and Charm
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

14. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
$1,575 nightly
The price is $1,580
Sep 29 - Sep 30
Total with taxes and fees
Molino In Chianti - Villa with Private Pool
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

15. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
$388 nightly
The price is $394
Sep 28 - Sep 29
Total with taxes and fees
Luxury Villa in the Florentine hills
A brick building with a gravel courtyard, a staircase, and potted plants.

16. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
$300 nightly
The price is $370
Oct 5 - Oct 6
Total with taxes and fees
GuestHost - Porta Romana Elegant House with Private Parking!
A covered balcony with a brick railing, a bench, and a view of lush greenery.

17. 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.
$664 nightly
The price is $664
Oct 2 - Oct 3
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.

18. 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
$4,909 nightly
The price is $4,912
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.

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
$1,301 nightly
The price is $1,306
Sep 28 - Sep 29
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.

20. 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.
$406 nightly
The price is $406
Sep 30 - Oct 1
Total with taxes and fees
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
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 Cavour

Grand Hotel Cavour

10/10 Excellent
"Excellent stay. Amazing front desk and clean and comfortable rooms. Very nice place!"
Catherine 2-night trip
Posted 1 hour ago
Grand Hotel Cavour

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
177
Accommodation
1829 Villas
Lowest Price
$149
Highest Price
$7,989

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $149 and $7,989 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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