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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Castellina in Chianti villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
$143 nightly
The price is $147
Oct 16 - Oct 17
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.

2. 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
$167 nightly
The price is $187
Oct 26 - Oct 27
Total with taxes and fees
Villa Montecastello
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.
$1,665 nightly
The price is $1,669
Nov 1 - Nov 2
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.
$2,038 nightly
The price is $2,043
Nov 3 - Nov 4
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.
$498 nightly
The price is $503
Oct 18 - Oct 19
Total with taxes and fees
Villa Il Signorino
A covered balcony with a brick railing, a bench, and a view of lush greenery.

6. 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.
$650 nightly
The price is $650
Nov 2 - Nov 3
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.

7. 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)
$3,051 nightly
The price is $3,051
Nov 8 - Nov 9
Total with taxes and fees
Villa Mami: A Tuscan Retreat of Elegance and Charm
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

8. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
$366 nightly
The price is $372
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa in the Florentine hills
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
$1,747 nightly
The price is $1,751
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
$1,747 nightly
The price is $1,751
Oct 17 - Oct 18
Total with taxes and fees
Villa Torre Among the Hills of Siena
A stone building with a large arched entrance, potted plants, and outdoor seating.

11. 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.
$1,244 nightly
The price is $1,249
Oct 19 - Oct 20
Total with taxes and fees
Exclusive Estate | Personal Concierge & Heated Pool
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

12. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
$2,152 nightly
The price is $2,157
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A villa with a swimming pool, surrounded by lush greenery and vineyards.

13. 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
$6,047 nightly
The price is $6,052
Oct 15 - Oct 16
Total with taxes and fees
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

14. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$14,534 nightly
The price is $14,534
Oct 17 - Oct 18
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A patio with a grill, a table, chairs, and a potted plant.

15. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
$1,079 nightly
The price is $1,082
Nov 2 - Nov 3
Total with taxes and fees
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
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.
$1,807 nightly
The price is $1,810
Nov 1 - Nov 2
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

17. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Montespertoli
10.0 out of 10, Exceptional, (12 reviews)
"Amazing Property! The house was impeccably clean, with spacious bedrooms and comfortable beds. Our gracious host Nicola spoiled us with his generosity. He went beyond our expectations to ensure that our stay was perfect. He and his wife welcomed us with a delicious homemade apple cake. He drove us to the nearby town of Montespertoli to pick-up groceries and provisions. He recommended a local chef to cook for us at the villa. The meal was amazing and memorable. We will be back!"
United States
Elise D.
$2,090 nightly
The price is $2,094
Nov 1 - Nov 2
Total with taxes and fees
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
A house with a covered patio, a lawn, and potted plants.

18. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
Reggello
$751 nightly
The price is $757
Nov 1 - Nov 2
Total with taxes and fees
Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
A person in a swimming pool with a view of a vineyard and hills.

19. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveler
$1,570 nightly
The price is $1,574
Oct 15 - Oct 16
Total with taxes and fees
"A Casa di Franca Villa con piscina"
A white shelving unit with various decorative items and framed pictures.

20. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
$674 nightly
The price is $677
Nov 2 - Nov 3
Total with taxes and fees
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
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

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"They have been very helpful with everything. And arranged several things for us while there"
Luci 2-night trip
Posted 5 hours ago
Grand Hotel Cavour

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
340
Accommodation
1829 Villas
Lowest Price
$147
Highest Price
$14,534

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $147 and $14,534 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