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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Castellina in Chianti villas

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
10.0 out of 10, Exceptional, (1 review)
"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 AED 677
AED 757 total
includes taxes & fees
24 Jun - 25 Jun
Villa Montecastello
Outdoor dining

Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (147 reviews)
"Beautiful property and great experience "
United States
edward p.
The price is AED 1,053
AED 1,660 total
includes taxes & fees
20 Jul - 21 Jul
Luxury Villa in the Florentine hills
Property grounds

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is AED 417
AED 506 total
includes taxes & fees
23 Jun - 24 Jun
Rooster House, cooking classes and opera
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is AED 2,999
AED 3,333 total
includes taxes & fees
24 Jun - 25 Jun
Villa Marcolina
Property grounds

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is AED 19,886
AED 21,993 total
includes taxes & fees
23 Jun - 24 Jun
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

The three owls of san gimignano

The three owls of san gimignano
San Gimignano
The price is AED 451
AED 536 total
includes taxes & fees
23 Jun - 24 Jun
The three owls of san gimignano
Exterior

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Oltrarno
10.0 out of 10, Exceptional, (1 review)
"Struttura a dir poco fantastica. Siamo stati non bene benissimo e sicuramente ci ritorneremo.Approfitto anche per fare un ringraziamento a Serena e Venita per l’immensa disponibilità, professionalità e cordialità ricevuta."
United States
Giuseppe F.
The price is AED 2,477
AED 3,219 total
includes taxes & fees
24 Jun - 25 Jun
NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!
Outdoor dining

Casa dei Renai by Rentbeat

Casa dei Renai by Rentbeat
Signa
The price is AED 235
AED 1,075 total
includes taxes & fees
7 Jul - 8 Jul
Casa dei Renai by Rentbeat
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is AED 1,327
AED 1,896 total
includes taxes & fees
23 Jun - 24 Jun
Villa Il Signorino
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is AED 1,911
AED 2,102 total
includes taxes & fees
23 Jun - 24 Jun
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
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 AED 39,772
AED 39,772 total
includes taxes & fees
26 Jun - 27 Jun
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AED 59,658
AED 59,658 total
includes taxes & fees
6 Jul - 7 Jul
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

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

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is AED 1,601
AED 1,609 total
includes taxes & fees
23 Jun - 24 Jun
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Exterior

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is AED 9,003
AED 10,364 total
includes taxes & fees
23 Jun - 24 Jun
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
Exterior

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is AED 1,955
AED 3,429 total
includes taxes & fees
24 Jun - 25 Jun
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
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)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is AED 1,261
AED 1,690 total
includes taxes & fees
23 Jun - 24 Jun
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Pool

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is AED 1,409
AED 1,590 total
includes taxes & fees
23 Jun - 24 Jun
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Outdoor dining

Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
Villa Capanna: A Window onto Tuscany
Terrace/patio

Golden Hour - wedding in Florence

Golden Hour - wedding in Florence
Toscana
The price is AED 11,586
AED 13,233 total
includes taxes & fees
29 Jun - 30 Jun
Golden Hour - wedding in Florence
Pool

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is AED 1,593
AED 1,774 total
includes taxes & fees
27 Jun - 28 Jun
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
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

Art Hotel Villa Agape

Art Hotel Villa Agape

10/10 Excellent
"This property is absolutely beautiful and amazing! If you want to relax while enjoying a beautiful scenic view, this is for you. If you want to walk around and explore, you can do that too. The staff are incredible and treated us very well. The shuttle to and from the hotel is a great amenity. The only complaint that we have is that the bedroom walls are a little thin and you can hear neighbors if you have them. Other than that, everything else about this place is awesome. It's up in the hills and out of the hustle and bustle of Florence and is quiet. We would absolutely stay here again."
Lonnie 4-night trip
Posted 2 hours ago
Art Hotel Villa Agape

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between AED 757 and AED 3,333 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 1908 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.