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Our top choices for Castellina in Chianti villas

1. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is ¥19,341
¥21,802 total
includes taxes & fees
Nov 4 - Nov 5
Rooster House, Cooking Classes, and Opera

2. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
The price is ¥104,984
¥189,537 total
includes taxes & fees
Nov 8 - Nov 9
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

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
The price is ¥55,913
¥62,032 total
includes taxes & fees
Nov 16 - Nov 17
Villa Montecastello

4. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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.
The price is ¥1,244,866
¥1,332,780 total
includes taxes & fees
Nov 3 - Nov 4
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

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.
The price is ¥269,018
¥273,238 total
includes taxes & fees
Nov 15 - Nov 16
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

6. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is ¥222,810
¥261,668 total
includes taxes & fees
Nov 3 - Nov 4
Villa Capanna: A Window onto Tuscany

7. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ¥222,810
¥261,668 total
includes taxes & fees
Nov 3 - Nov 4
Villa Torre Among the Hills of Siena

8. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is ¥351,657
¥458,033 total
includes taxes & fees
Nov 3 - Nov 4
Villa Mami: A Tuscan retreat full of elegance and charm

9. 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
The price is ¥949,474
¥950,177 total
includes taxes & fees
Nov 3 - Nov 4
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

10. 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.
The price is ¥182,948
¥204,392 total
includes taxes & fees
Nov 3 - Nov 4
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

11. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is ¥2,489,733
¥2,489,733 total
includes taxes & fees
Nov 3 - Nov 4
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

12. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is ¥1,659,822
¥1,659,822 total
includes taxes & fees
Nov 3 - Nov 4
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

13. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (117 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.
The price is ¥153,850
¥176,532 total
includes taxes & fees
Nov 3 - Nov 4
Exclusive Estate | Personal Concierge & Heated Pool

14. 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.
The price is ¥228,577
¥248,797 total
includes taxes & fees
Nov 29 - Nov 30
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
The price is ¥506,386
¥874,747 total
includes taxes & fees
Nov 3 - Nov 4
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

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.
The price is ¥284,842
¥285,194 total
includes taxes & fees
Nov 4 - Nov 5
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

17. 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
The price is ¥181,736
¥182,263 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

18. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
Toscana
The price is ¥351,657
¥382,427 total
includes taxes & fees
Nov 3 - Nov 4
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

19. 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.
The price is ¥290,117
¥328,799 total
includes taxes & fees
Nov 3 - Nov 4
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

20. "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
The price is ¥182,262
¥268,560 total
includes taxes & fees
Nov 3 - Nov 4
"A Casa di Franca Villa con piscina"
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

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
191
Accommodation
1812 Villas
Lowest Price
¥21,802
Highest Price
¥2,489,733

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between ¥21,802 and ¥2,489,733 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 1812 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.