Title: Chianti Region Villas from CA $129 | Expedia.ca

[Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[Chianti Region Vacation Packages](https://expedia.ca/Chianti-Region.d603148.Destination-Travel-Guides)

![Typical Tuscany stone house with vineyard in the Chianti region and magical sunset,Tuscany,Italy,Europe; Shutterstock ID 230998399](https://images.trvl-media.com/place/603148/f55ed247-c704-412c-bed7-4bc776c30e02.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/603148/f55ed247-c704-412c-bed7-4bc776c30e02.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=603148&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chianti Region villas

![Pool](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/dcfa042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/52aa6660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/afb73a16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33070000/33066500/33066451/25aedd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

CA $9,620

CA $10,429 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-CHIANTIGAIO-Fourteen-Bedroom-Villa.h33066451.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a34e800d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/a26a2615.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/52fb9f8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/34000000/33960000/33956800/33956712/65e72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles S.

CA $1,305

CA $1,486 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Impruneta-Hotels-Tailored-To-YouVilla-Wheated-Pool-And-Concierge-Only-8-Mile-To-Florence-Center.h33956712.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/1e6c21a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/c326d5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/9fd29a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78170000/78165700/78165677/2fd0fef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott M.

CA $2,590

CA $2,593 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Montespertoli-Hotels-Villa-Milani-With-Shared-Pool.h78165677.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/b8286297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/03ae69bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/4a362287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99440000/99430700/99430681/513cbcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Radda in Chianti

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/pl.svg)

Anonymous traveller

CA $2,839

CA $3,872 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Radda-In-Chianti-Hotels-Villa-La-Petrosa-With-Private-Pool.h99430681.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/c3424e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/368811a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/ecc6720f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123670000/123669300/123669271/8b48796e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information)

CA $517

CA $1,050 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-Viniard-Villa-Residence-Le-Rose-In-Chianti.h123669271.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/38e5a789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h863x2y0-ddee714e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h854x2y0-790f85bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108280000/108275300/108275238/w1166h857x2y0-a94584e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Impruneta

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lidija M.

CA $562

CA $711 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Impruneta-Hotels-Vrbo-Property.h108275238.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/bd7589fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/62d8efb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/57f40b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86500000/86496800/86496746/87d9fa0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Florence

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

10/10

Exceptional

(6 reviews)

"Judy was amazing and very helpfulNothing to do with the property, but I sure you pre book all nights out/transportation"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frank V.

CA $1,048

CA $1,935 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Beautiful-Tuscan-Home-Between-Florence-Siena.h86496746.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/60af890d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/912c9501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/a6e7b444.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99790000/99787300/99787239/f69f21a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Rignano sull'Arno

[](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information)

7.0/10

Good

(2 reviews)

"We arrived after dark, tired from long overnight flight. We had no water pressure upstairs and no hot water anywhere. This was corrected the next day. One on-suite toilette would not flush properly and leaked at the grinder motor. A "tech" was called in. He informed us that he could not fix it, they would need to call someone else. When we continued to report the issue to the host, she informed us that the "tech" said it was working OK. The "tech" informed us that it was not but he could not fix...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Norman C.

CA $3,748

CA $4,642 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Rignano-SullArno-Hotels-Villa-Il-Frassine-With-Private-Pool.h99787239.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/c92c20b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/aa63342e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/4b9923b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122490000/122488700/122488659/b48487ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Colle Val D'Elsa

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

CA $19,079

CA $19,079 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Colle-Di-Val-DElsa-Hotels-VILLA-ALTAMIRA-Eighteen-Bedroom-Villa.h122488659.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/w1920h1279x0y1-a132bf6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/09d64836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, free WiFi](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/0a5c24e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76780000/76771500/76771413/bc5dd1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Castellina in Chianti

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

CA $7,600

CA $8,408 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Castellina-In-Chianti-Hotels-VILLA-IL-PRINCIPE-Nine-Bedroom-Villa.h76771413.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/w2189h1640x4y5-0fbf58c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/51bd2610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/09a8ec09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32590000/32584300/32584249/87c073f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elise D.

CA $2,070

CA $2,361 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury.h32584249.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/06053989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/08415ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/682c69f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/32000000/31540000/31539100/31539094/37bf79c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montespertoli

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

10/10

Exceptional

(38 reviews)

"Excellent in every way. Highly recommend"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ed M.

CA $2,102

CA $2,398 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Montespertoli-Hotels-Luxury-Villa-With-Swimmingpool-In-Chianti-Sleeps-22-Large-Groups.h31539094.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/81953563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/0e2eec35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/ae2c6602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83210000/83207300/83207211/a822b4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Gaiole in Chianti

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

10/10

Exceptional

(8 reviews)

"Country location but easy access to a great local winery/restaurant and the town of Gaiole."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

russ h.

CA $1,681

CA $1,720 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Gaiole-In-Chianti-Hotels-Villa-Erbolino-With-Private-Garden.h83207211.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/9dbd198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/99750750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/09f4ffea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292182/59636b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

[](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information)

CA $1,557

CA $1,717 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Siena-Hotels-Villa-Capannina-With-Private-Pool.h123292182.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/7dec8a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/2e9c5263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/e3bba8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292187/717cdd46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

[](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information)

CA $2,194

CA $2,354 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Siena-Hotels-Villa-Torre-Among-The-Hills-Of-Siena.h123292187.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/5657bedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/24bd1fb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/3b5e29fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114510000/114506600/114506575/538ab53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Tavarnelle Val di Pesa

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information)

CA $1,757

CA $2,191 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Barberino-Tavarnelle-Hotels-Villa-Virgilio-Colline-Del-Chianti-With-Mountain-View.h114506575.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/798e008d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/b1163ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b99bc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/124000000/123300000/123292200/123292181/1b3afdb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Vico dʼArbia

[](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information)

CA $2,194

CA $2,354 total

includes taxes & fees

Jan 17 - Jan 18

[](https://www.expedia.ca/Siena-Hotels-Villa-Capanna-A-Window-Onto-Tuscany.h123292181.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/8208f9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Triple Room | Bathroom](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/4f173bce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Foiano della Chiana

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

8.4/10

Very good

(24 reviews)

"Good house for one night. "

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Heiner

CA $114

CA $129 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d05582b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Sinalunga

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

10/10

Exceptional

(59 reviews)

"Fantastic place! Great location. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Paul Q.

CA $240

CA $276 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/b93cd03b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/289988b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/2eb34797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/34000000/33320000/33313600/33313600/663d28a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Siena

[](https://www.expedia.ca/Siena-Hotels-VILLA-ASCARA-Fifteen-Bedroom-Villa.h33313600.Hotel-Information)

CA $7,696

CA $8,505 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Siena-Hotels-VILLA-ASCARA-Fifteen-Bedroom-Villa.h33313600.Hotel-Information)

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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## Find vacation rentals that suit your style

Villas

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Private vacation homes

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Condos

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Cabins

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## Top Chianti Region Hotel Reviews

![Villa Casagrande Resort & SPA](https://images.trvl-media.com/lodging/1000000/900000/891700/891661/f41faf16_y.jpg)

### Villa Casagrande Resort & SPA

10/10 Excellent

"Always beautiful when I stay here, staff are helpful and every room clean and tidy "

[](https://expedia.ca/Figline-E-Incisa-Valdarno-Hotels-Villa-Casagrande-Resort-SPA.h891661.Hotel-Information)

![Hotel Palazzo San niccolò & Spa](https://images.trvl-media.com/lodging/2000000/1290000/1289200/1289163/b8b0f4e2_y.jpg)

### Hotel Palazzo San niccolò & Spa

10/10 Excellent

"One of the best hotels I’ve visited! "

[](https://expedia.ca/Radda-In-Chianti-Hotels-Hotel-Palazzo-San-Niccolo.h1289163.Hotel-Information)

![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg)

### Hotel Borgo di Cortefreda Relais

10/10 Excellent

"The hotel and services exceeded my expectations."

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-Hotel-Borgo-Di-Cortefreda-Relais.h1216478.Hotel-Information)

![Hotel Toscana Ambassador](https://images.trvl-media.com/lodging/2000000/1430000/1429500/1429488/7717f75b_y.jpg)

### Hotel Toscana Ambassador

10/10 Excellent

"We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, stay here with no hesitation. "

[](https://expedia.ca/Poggibonsi-Hotels-Hotel-Toscana-Ambassador.h1429488.Hotel-Information)

![Salvadonica - Borgo del Chianti](https://images.trvl-media.com/lodging/21000000/20490000/20484000/20483959/56ce48bb_y.jpg)

### Salvadonica - Borgo del Chianti

10/10 Excellent

"Great staff, great room and amenities. Outstanding romantic Tuscany location. Going back again."

[](https://expedia.ca/San-Casciano-In-Val-Di-Pesa-Hotels-Salvadonica.h20483959.Hotel-Information)

![Castello Vicchiomaggio](https://images.trvl-media.com/lodging/8000000/7570000/7564900/7564854/3167b59e_y.jpg)

### Castello Vicchiomaggio

10/10 Excellent

"This beautiful property stole our hearts back in 2019, when my now-wife first visited this magical place. Six years later, we returned — this time to celebrate our wedding reception after tying the knot a few months earlier. From start to finish, everything was beyond wonderful. A special mention to Sandra, the amazing coordinator who made everything run so smoothly, and her fantastic team — Delfina and the lovely lady (whose name, unfortunately, I’ve forgotten) who graciously welcomed and ushered our guests upon arrival. Every detail was handled with care and professionalism. The food and Chianti wines during our celebration were absolutely exceptional — truly a highlight that everyone still talks about! The breakfast and dinner staff were attentive, kind, and ensured everything was perfect throughout our stay. Our rooms were clean, comfortable, and beautifully maintained, with housekeeping doing a fantastic job. We also had the privilege of meeting Mr. John Matta, the owner — such a gracious and inspiring man who leads an extraordinary team. All of our guests loved their stay, and we left with hearts full of joy and gratitude. We can’t wait to come back again — hopefully for our anniversary next time."

[](https://expedia.ca/Greve-In-Chianti-Hotels-Castello-Vicchiomaggio.h7564854.Hotel-Information)

![Villa Castiglione](https://images.trvl-media.com/lodging/2000000/1350000/1348200/1348125/dbdc1d6b_y.jpg)

### Villa Castiglione

10/10 Excellent

"Nice and cute place. Great price. "

[](https://expedia.ca/Impruneta-Hotels-Villa-Castiglione.h1348125.Hotel-Information)

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg)

### COMO Castello Del Nero

10/10 Excellent

"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "

[](https://expedia.ca/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information)

![Il Borro - Relais & Châteaux](https://images.trvl-media.com/lodging/6000000/5590000/5585700/5585638/4a6bd899_y.jpg)

### Il Borro - Relais & Châteaux

10/10 Excellent

"A one of a kind, unique property amazing cuisine, and the tour we took of the wine cellar was the best I have ever experienced thanks to the helpfulness and knowledge of our guide Sophia"

[](https://expedia.ca/Loro-Ciuffenna-Hotels-Il-Borro-Relais-Chateaux.h5585638.Hotel-Information)

## Find out more about Chianti Region

## Chianti Region Villas information

| Number of reviews | 224        |
| ----------------- | ---------- |
| Accommodation     | 571 Villas |
| Lowest Price      | CA $129    |
| Highest Price     | CA $10,429 |

## Frequently asked questions

### How much do villas in Chianti Region cost?

### How many villas are there in Chianti Region?

### Why book your villa in Chianti Region with Expedia?

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- [Farmstay in San Casciano in Val di Pesa ](https://www.expedia.ca/San-Casciano-In-Val-Di-Pesa-Agritourism.d6047590-aaAgritourism.Travel-Guide-Accommodation)
- [San Donato in Poggio Hotels ](https://www.expedia.ca/San-Donato-In-Poggio-Hotels.d6292835.Travel-Guide-Hotels)
- [Castles in Santo Stefano A Tizzano ](https://www.expedia.ca/Santo-Stefano-A-Tizzano-Castles.d3000026316-aaCastles.Travel-Guide-Accommodation)
- [Sicelle Hotels ](https://www.expedia.ca/Sicelle-Hotels.d6343024.Travel-Guide-Hotels)
- [Farmstay in Siena ](https://www.expedia.ca/Siena-Agritourism.d9821-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Siena ](https://www.expedia.ca/Siena-Apart-Hotels.d9821-aaApartHotels.Travel-Guide-Accommodation)
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- [Vacation Homes in Siena ](https://www.expedia.ca/Siena-Private-Vacation-Homes.d9821-aaPrivateVacationHomes.Travel-Guide-Accommodation)
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- [Resorts in Siena ](https://www.expedia.ca/Siena-Resort-Hotels.d9821-aaResortHotels.Travel-Guide-Accommodation)
- [Townhomes in Siena ](https://www.expedia.ca/Siena-Townhomes.d9821-aaTownhomes.Travel-Guide-Accommodation)
- [Villas in Siena ](https://www.expedia.ca/Siena-Villas.d9821-aaVillas.Travel-Guide-Accommodation)
- [Villas in Tavarnelle Val di Pesa ](https://www.expedia.ca/Tavarnelle-Val-Di-Pesa-Villas.d6023366-aaVillas.Travel-Guide-Accommodation)
- [Vertine Hotels ](https://www.expedia.ca/Vertine-Hotels.d632712480144572416.Travel-Guide-Hotels)
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- [Volpaia Hotels ](https://www.expedia.ca/Volpaia-Hotels.d3000403024.Travel-Guide-Hotels)

- [Flights to Castellina in Chianti ](https://www.expedia.ca/Cheap-Flights-To-Castellina-In-Chianti.d55534.Travel-Guide-Flights)
- [Flights to Gaiole in Chianti ](https://www.expedia.ca/Cheap-Flights-To-Gaiole-In-Chianti.d603149.Travel-Guide-Flights)
- [Flights to San Donato in Poggio ](https://www.expedia.ca/Cheap-Flights-To-San-Donato-In-Poggio.d6292835.Travel-Guide-Flights)
- [Flights from Castellina in Chianti ](https://www.expedia.ca/lp/flights/55534/flights-from-castellina-in-chianti)
- [Flights from Gaiole in Chianti ](https://www.expedia.ca/lp/flights/603149/flights-from-gaiole-in-chianti)

- [Buondonno Winery ](https://www.expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction)
- [Casa Vinicola Luigi Cecchi ](https://www.expedia.ca/Casa-Vinicola-Luigi-Cecchi-Castellina-in-Chianti.d6103262.Vacation-Attraction)
- [Visit Castelnuovo dei Sabbioni ](https://www.expedia.ca/Castelnuovo-Dei-Sabbioni.dx602580)
- [Church of San Sigismondo ](https://www.expedia.ca/Church-Of-San-Sigismondo-Gaiole-in-Chianti.d6238140.Vacation-Attraction)
- [Visit Gaiole in Chianti ](https://www.expedia.ca/Gaiole-In-Chianti.dx603149)
- [Visit Greve in Chianti ](https://www.expedia.ca/Greve-In-Chianti.dx601773)
- [Visit Meleto ](https://www.expedia.ca/Meleto.dx6292517)
- [Visit Montefioralle ](https://www.expedia.ca/Montefioralle.dx3000404943)
- [Visit Panzano in Chianti ](https://www.expedia.ca/Panzano-In-Chianti.dx602564)
- [Visit Ponte Agli Stolli ](https://www.expedia.ca/Ponte-Agli-Stolli.dx6342228)
- [Visit Radda in Chianti ](https://www.expedia.ca/Radda-In-Chianti.dx601693)
- [Visit San Donato in Poggio ](https://www.expedia.ca/San-Donato-In-Poggio.dx6292835)
- [Visit Sicelle ](https://www.expedia.ca/Sicelle.dx6343024)
- [Visit Vertine ](https://www.expedia.ca/Vertine.dx632712480144572416)

- [Car rental Castellina in Chianti ](https://www.expedia.ca/Car-Rentals-In-Castellina-In-Chianti.d55534.Car-Rental-Guide)
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- [Car rental Panzano in Chianti ](https://www.expedia.ca/Car-Rentals-In-Panzano-In-Chianti.d602564.Car-Rental-Guide)
- [Car rental Radda in Chianti ](https://www.expedia.ca/Car-Rentals-In-Radda-In-Chianti.d601693.Car-Rental-Guide)

- [Things to do in Fonterutoli ](https://www.expedia.ca/Things-To-Do-In-Fonterutoli.d6342141.Travel-Guide-Activities)
- [Things to do in Gaiole in Chianti ](https://www.expedia.ca/Things-To-Do-In-Gaiole-In-Chianti.d603149.Travel-Guide-Activities)
- [Things to do in Greve in Chianti ](https://www.expedia.ca/Things-To-Do-In-Greve-In-Chianti.d601773.Travel-Guide-Activities)
- [Things to do in Lecchi in Chianti ](https://www.expedia.ca/Things-To-Do-In-Lecchi-In-Chianti.d553248635974650979.Travel-Guide-Activities)
- [Things to do in Panzano in Chianti ](https://www.expedia.ca/Things-To-Do-In-Panzano-In-Chianti.d602564.Travel-Guide-Activities)

- [Book Villas in Chianti Region on Expedia.it ](https://www.expedia.it/Regione-Del-Chianti-Ville.d603148-aaVille.Guida-Viaggi-Alloggi)