A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Castellina in Chianti villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
The price is AU$199
includes taxes & fees
3 Nov - 4 Nov
Rooster House, Cooking Classes, and Opera
A stone building with a swimming pool, wooden deck, and a tall tree.

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 AU$1,711
includes taxes & fees
8 Nov - 9 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

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 AU$560
includes taxes & fees
15 Nov - 16 Nov
Villa Montecastello
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

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 AU$12,029
includes taxes & fees
3 Nov - 4 Nov
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

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 AU$2,466
includes taxes & fees
15 Nov - 16 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

6. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AU$2,362
includes taxes & fees
4 Nov - 5 Nov
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

7. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AU$2,362
includes taxes & fees
3 Nov - 4 Nov
Villa Torre Among the Hills of Siena
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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 AU$3,955
includes taxes & fees
8 Nov - 9 Nov
Villa Mami: A Tuscan retreat full of elegance and charm
A villa with a swimming pool, surrounded by lush greenery and vineyards.

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 AU$8,576
includes taxes & fees
3 Nov - 4 Nov
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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 AU$1,845
includes taxes & fees
3 Nov - 4 Nov
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

11. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AU$22,472
includes taxes & fees
3 Nov - 4 Nov
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

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 AU$14,981
includes taxes & fees
4 Nov - 5 Nov
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A stone building with a large arched entrance, potted plants, and outdoor seating.

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 AU$1,582
includes taxes & fees
3 Nov - 4 Nov
Exclusive Estate | Personal Concierge & Heated Pool
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

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 AU$2,185
includes taxes & fees
29 Nov - 30 Nov
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

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 AU$7,643
includes taxes & fees
3 Nov - 4 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A building with a large entrance, potted plants, and a statue in the foreground.

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 AU$2,574
includes taxes & fees
3 Nov - 4 Nov
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

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 AU$1,645
includes taxes & fees
3 Nov - 4 Nov
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A courtyard with a building, potted plants, and a grassy area.

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 AU$3,303
includes taxes & fees
3 Nov - 4 Nov
SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms
A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

19. Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco

Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
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 AU$2,909
includes taxes & fees
3 Nov - 4 Nov
Luxury,Charming,in true Chianti, sleeps 21 or +people with Sw-Pool,Wi-Fi,Airco
A person in a swimming pool with a view of a vineyard and hills.

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 traveller
The price is AU$2,424
includes taxes & fees
3 Nov - 4 Nov
"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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Great convenient stay! We stayed with 3 kids. Perfect stay if you plan on spending most of your days sightseeing. Bus into town located directly across the road. Beds comfy enough..prob the easiest check in we have experienced so far.. definitely recommend. Super popular with many campers in vans and tents. The restaurant is super popular - American style fair - go into town for pasta - the pizzas and burgers were super popular. There are washing machines that work great. The dryers are hit and miss. The units are very clean. All in all woukd recommend for a family stay."
Warren 4-night trip
Posted 7 hours ago
Hu Firenze Camping In Town

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
191
Accommodation
1530 Villas
Lowest Price
AU$199
Highest Price
AU$22,472

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Prepare to pay between AU$199 and AU$22,472 per night for a villa in Castellina in Chianti. No matter your budget, a perfect stay is only a few clicks away on Expedia. This price was 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?
Lock in your holiday dates and then choose from 1530 villas in Castellina in Chianti. For a family trip, a couple's getaway and everything in between, Expedia can help you find the perfect space in a few easy clicks.
What is there to do near my villa in Castellina in Chianti?
Castellina in Chianti has enough activities and experiences to keep you on the go for weeks (or months!), starting with Monteriggioni Castle. Meleto Castle, Castello di Radda Winery and Castello di Albola are other impressive attractions. If you're hanging around a while, Badia a Coltibuono and Isole e Olena Winery will add the finishing touches to your itinerary.