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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Castellina in Chianti villas

Pool
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

Villa in Castellina in Chianti

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
The price is ￥868,272
￥960,631 total
includes taxes & fees
Jan 2 - Jan 3, 2026
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Terrace/patio
Viniard Villa - Residence Le Rose in Chianti

Villa in Castellina in Chianti

Viniard Villa - Residence Le Rose in Chianti
The price is ￥59,110
￥121,065 total
includes taxes & fees
Dec 25 - Dec 26
Viniard Villa - Residence Le Rose in Chianti
Exterior
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Villa in Careggi Rifredi

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
10.0 out of 10, Exceptional, (1)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
The price is ￥1,758,525
￥1,758,525 total
includes taxes & fees
Dec 22 - Dec 23
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Pool
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

Villa in Gaiole in Chianti

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
The price is ￥1,099,078
￥1,191,437 total
includes taxes & fees
Dec 22 - Dec 23
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Pool
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa in Radda in Chianti

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
10.0 out of 10, Exceptional, (1)
"Pros: Świetna lokalizacja i przyjemne otoczenie domu. Dom położony na wzniesieniu z którego roztaczał się piękny widok. Cons: Osoba opiekująca się domem nie mówiła po angielsku co utrudniało komunikację. Nie byliśmy świadomi że dom podzielony jest na 2 części góra i piwnica w której były dodatkowe 3 pokoje. Uszkodzona pralka która nie dopierała pranych ubrań - brudna woda z zanieczyszczeniami które dodatkowo brudziły ubrania."
Poland
Anonymous traveler
The price is ￥297,353
￥415,329 total
includes taxes & fees
Dec 23 - Dec 24
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Pool
panoramica casa con piscina privata

Villa in siena

panoramica casa con piscina privata
7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
United Kingdom
Olivier B.
panoramica casa con piscina privata
Pool
Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa in Montespertoli

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
10.0 out of 10, Exceptional, (1)
"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 ￥299,245
￥299,614 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Villa in Colle Val D'Elsa

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
The price is ￥2,179,684
￥2,179,684 total
includes taxes & fees
Dec 22 - Dec 23
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Outdoor dining
Tuscany Garden Villa

Villa in Figline Valdarno

Tuscany Garden Villa
10.0 out of 10, Exceptional, (2)
"Rymligt hus med bra toaletter! Väl utrustat kök. Saknade dock ac i ett av sovrummen"
Sweden
Gertrud R.
The price is ￥64,652
￥92,914 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Tuscany Garden Villa
Garden
Wine Apartments Florence Lawrence

Villa in Scandicci

Wine Apartments Florence Lawrence
The price is ￥8,396
￥51,535 total
includes taxes & fees
Dec 23 - Dec 24
Wine Apartments Florence Lawrence
Exterior
Villa "Arnilù" with Private Pool & Wi-Fi

Villa in San Gimignano

Villa "Arnilù" with Private Pool & Wi-Fi
The price is ￥857,818
￥926,323 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining
Casa dei Renai by Rentbeat

Villa in Signa

Casa dei Renai by Rentbeat
The price is ￥8,176
￥44,518 total
includes taxes & fees
Dec 22 - Dec 23
Casa dei Renai by Rentbeat
Outdoor spa tub
Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa in Toscana

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
10.0 out of 10, Exceptional, (1)
"The host was amazing! The property was beautiful. All was seamless! All of our needs were met. Highly recommend! "
United States
Leopard I.
The price is ￥329,169
￥376,088 total
includes taxes & fees
Dec 22 - Dec 23
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Property grounds
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Villa in Gaiole in Chianti

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
10.0 out of 10, Exceptional, (8)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is ￥103,073
￥107,506 total
includes taxes & fees
Dec 22 - Dec 23
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior
Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa in Rapolano Terme

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
9.0 out of 10, Wonderful, (4)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is ￥115,339
￥161,133 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior
Country House with heated pool near the center

Villa in Careggi Rifredi

Country House with heated pool near the center
9.4 out of 10, Exceptional, (10)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
United States
Nancy P.
The price is ￥55,416
￥87,927 total
includes taxes & fees
Dec 23 - Dec 24
Country House with heated pool near the center
Exterior
Beautiful Tuscan home between Florence & Siena

Villa in Florence

Beautiful Tuscan home between Florence & Siena
10.0 out of 10, Exceptional, (6)
"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"
United States
Frank V.
The price is ￥132,998
￥236,441 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Beautiful Tuscan home between Florence & Siena
Pool
"A Casa di Franca Villa con piscina"

Villa in Gambassi Terme

"A Casa di Franca Villa con piscina"
10.0 out of 10, Exceptional, (1)
"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 ￥137,414
￥205,549 total
includes taxes & fees
Dec 23 - Dec 24
"A Casa di Franca Villa con piscina"
Exterior
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Villa in Montespertoli

Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
10.0 out of 10, Exceptional, (12)
"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 ￥236,440
￥270,798 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!
Exterior
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Villa in Montespertoli

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
United States
Ed M.
The price is ￥240,135
￥275,047 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites
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

Hotel Spadai

Hotel Spadai

10/10 Excellent
"Staff was very accommodating will definitely recommend this hotel."
Frank 2-night trip
Posted 2 days ago
Hotel Spadai

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
55
Accommodation
1968 Villas
Lowest Price
￥44,518
Highest Price
￥1,758,525

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between ￥44,518 and ￥1,758,525 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 1968 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.