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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$168 nightly
The price is $188
Oct 4 - Oct 5
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
$144 nightly
The price is $147
Oct 5 - Oct 6
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.
$1,799 nightly
The price is $1,804
Nov 1 - Nov 2
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
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.

4. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$504 nightly
The price is $508
Oct 6 - Oct 7
Total with taxes and fees
Villa Il Signorino
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 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.
$782 nightly
The price is $786
Oct 5 - Oct 6
Total with taxes and fees
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

6. 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.
$7,887 nightly
The price is $7,887
Oct 5 - Oct 6
Total with taxes and fees
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

7. 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.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
$5,965 nightly
The price is $5,971
Oct 5 - Oct 6
Total with taxes and fees
Villa "Arnilù" with Private Pool & Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

9. 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.
$656 nightly
The price is $656
Oct 4 - Oct 5
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

10. 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)
$3,073 nightly
The price is $3,073
Oct 18 - Oct 19
Total with taxes and fees
Villa Mami: A Tuscan Retreat of Elegance and Charm
A two-story building with a garden, a gazebo, and a statue.

11. 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
$4,846 nightly
The price is $4,849
Oct 7 - Oct 8
Total with taxes and fees
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

12. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,827 nightly
The price is $1,832
Nov 2 - Nov 3
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

13. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,827 nightly
The price is $1,832
Nov 2 - Nov 3
Total with taxes and fees
Villa Torre Among the Hills of Siena
A villa with a swimming pool, surrounded by lush greenery and vineyards.

14. 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
$6,747 nightly
The price is $6,751
Oct 14 - Oct 15
Total with taxes and fees
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
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.
$364 nightly
The price is $370
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa in the Florentine hills
A building with a large entrance, potted plants, and a statue in the foreground.

16. 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.
$2,024 nightly
The price is $2,026
Nov 1 - Nov 2
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$14,649 nightly
The price is $14,649
Oct 6 - Oct 7
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

18. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
$1,555 nightly
The price is $1,560
Oct 6 - Oct 7
Total with taxes and fees
Molino In Chianti - Villa with Private Pool
A stone building with a large arched entrance, potted plants, and outdoor seating.

19. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
$1,227 nightly
The price is $1,232
Oct 26 - Oct 27
Total with taxes and fees
Exclusive Estate | Personal Concierge & Heated Pool
Pool

20. 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
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Once you get to the property the staff were all wonderful but the communication prior to arrival was none no answers to any of my questions through Expedia. The city bus is across the street takes you into Florence for 2 euros but make sure you validate your ticket front of bus to avoid a hefty fine. I loved that we could cook breakfast before heading out and there is a grocery store onsite."
tina 3-night trip
Posted 7 hours ago
Hu Firenze Camping In Town

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
286
Accommodation
1829 Villas
Lowest Price
$147
Highest Price
$14,649

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $147 and $14,649 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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