Search Villas in Castellina in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Castellina in Chianti villas

Pool

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥766,662
￥857,274 total
includes taxes & fees
Feb 28 - Mar 1
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Terrace/patio

Viniard Villa - Residence Le Rose in Chianti

Viniard Villa - Residence Le Rose in Chianti
Castellina in Chianti
The price is ￥57,992
￥118,050 total
includes taxes & fees
Feb 21 - Feb 22
Viniard Villa - Residence Le Rose in Chianti
Pool

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28

CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Gaiole in Chianti
The price is ￥970,459
￥1,061,071 total
includes taxes & fees
Feb 20 - Feb 21
CHIANTIGAIO - Fourteen Bedroom Villa, Sleeps 28
Exterior

Country House with heated pool near the center

Country House with heated pool near the center
Careggi Rifredi
9.4 out of 10, Exceptional, (10 reviews)
"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 ￥39,869
￥69,408 total
includes taxes & fees
Feb 17 - Feb 18
Country House with heated pool near the center
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is ￥776,367
￥866,979 total
includes taxes & fees
Feb 26 - Feb 27
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is ￥1,924,607
￥1,924,607 total
includes taxes & fees
Feb 22 - Feb 23
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Property grounds

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is ￥498,368
￥569,227 total
includes taxes & fees
Feb 19 - Feb 20
Golden Hour - wedding in Florence
Exterior

Villa w/ personal concierge service, heated pool only 20 min to Florence center

Villa w/ personal concierge service, heated pool only 20 min to Florence center
impruneta
10.0 out of 10, Exceptional, (106 reviews)
"The Villa and grounds are absolutely beautiful! Caterina and her family members were the most gracious hosts. They could not do enough to make sure we had a "once in a lifetime" multi-generational family trip and truly made us feel like part of their family during our stay. We loved every second of our time in Tuscany and would highly recommend this amazing property."
United States
Charles S.
The price is ￥206,877
￥237,142 total
includes taxes & fees
Feb 23 - Feb 24
Villa w/ personal concierge service, heated pool only 20 min to Florence center
Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8 reviews)
"Country location but easy access to a great local winery/restaurant and the town of Gaiole."
Canada
russ h.
The price is ￥271,837
￥276,186 total
includes taxes & fees
Mar 13 - Mar 14
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"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 ￥113,157
￥158,085 total
includes taxes & fees
Feb 22 - Feb 23
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Pool

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, (1 review)
"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 ￥318,249
￥433,994 total
includes taxes & fees
Feb 19 - Feb 20
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Exterior

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 ￥1,552,734
￥1,552,734 total
includes taxes & fees
Feb 18 - Feb 19
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Exterior

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
The price is ￥156,904
￥174,845 total
includes taxes & fees
Feb 17 - Feb 18
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Outdoor dining

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)
"Pictures do not do it justice, this house and location is absolutely beautiful. Very comfortable beds, clean house, beauty views, nice fireplace.owner goes above and beyond to make you feel welcome. She had her local wine, cooked us a delishes breakfast, and also brought her olive oil to do tasting. We will definitely be back, i thank you for an amazing experience and a beautiful house."
United States
Lidija M.
The price is ￥62,994
￥80,573 total
includes taxes & fees
Feb 17 - Feb 18
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Pool

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 ￥290,322
￥290,684 total
includes taxes & fees
Feb 18 - Feb 19
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Exterior

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Siena
The price is ￥58,717
￥59,079 total
includes taxes & fees
Feb 17 - Feb 18
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi and Air Conditioning
Exterior

Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥221,167
￥239,108 total
includes taxes & fees
Feb 17 - Feb 18
Villa Torre Among the Hills of Siena
Outdoor spa tub

Villa Dei Pavoni - Luxury Villa on top of hills in Florence

Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Toscana
10.0 out of 10, Exceptional, (1 review)
"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 ￥322,943
￥367,343 total
includes taxes & fees
Feb 17 - Feb 18
Villa Dei Pavoni - Luxury Villa on top of hills in Florence
Exterior

Beautiful Tuscan home between Florence & Siena

Beautiful Tuscan home between Florence & Siena
Florence
10.0 out of 10, Exceptional, (7 reviews)
"From the moment we entered to our last day everything was perfect. Group of 15 and we all fit comfortably. "
United States
Debra P.
The price is ￥161,471
￥266,763 total
includes taxes & fees
Feb 17 - Feb 18
Beautiful Tuscan home between Florence & Siena
Exterior

Dante's Paradise with a View of Florence

Dante's Paradise with a View of Florence
Careggi Rifredi
The price is ￥65,241
￥85,538 total
includes taxes & fees
Feb 17 - Feb 18
Dante's Paradise with a View of Florence
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

Orto De Medici Hotel

Orto De Medici Hotel

10/10 Excellent
"The staff was great, the room was very nice and the breakfast was delicious! "
Joseph 1-night trip
Posted 3 days ago
Orto De Medici Hotel

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
133
Accommodation
1969 Villas
Lowest Price
￥69,408
Highest Price
￥1,552,734

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between ￥69,408 and ￥1,552,734 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 1969 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.