Castellina in Chianti Villas ￥21,802

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

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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

Tavarnelle Val di Pesa

￥21,802 total

includes taxes & fees

Nov 4 - Nov 5

A stone building with a swimming pool, wooden deck, and a tall tree.

2. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

"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...

JIm B.

￥189,537 total

includes taxes & fees

Nov 9 - Nov 10

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

3. Villa Montecastello

Monteriggioni

Alvaro

￥62,043 total

includes taxes & fees

Nov 15 - Nov 16

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

Siena

Ron M.

￥1,332,780 total

includes taxes & fees

Nov 3 - Nov 4

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

Gaiole in Chianti

Bernard K.

￥273,238 total

includes taxes & fees

Nov 15 - Nov 16

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

Vico dʼArbia

￥261,668 total

includes taxes & fees

Nov 3 - Nov 4

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

7. Villa Torre Among the Hills of Siena

Vico dʼArbia

￥261,668 total

includes taxes & fees

Nov 3 - Nov 4

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

Toscana

￥458,033 total

includes taxes & fees

Nov 3 - Nov 4

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

Montespertoli

￥950,177 total

includes taxes & fees

Nov 3 - Nov 4

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

Certaldo - Firenze

Kelly C.

￥204,392 total

includes taxes & fees

Nov 3 - Nov 4

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

Firenze

￥2,489,733 total

includes taxes & fees

Nov 3 - Nov 4

A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

12. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Careggi Rifredi

robert g.

￥1,659,822 total

includes taxes & fees

Nov 3 - Nov 4

A stone building with a large arched entrance, potted plants, and outdoor seating.

13. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Oli P.

￥176,532 total

includes taxes & fees

Nov 3 - Nov 4

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

Montespertoli

Krista G.

￥248,797 total

includes taxes & fees

Nov 29 - Nov 30

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

Rignano sull'Arno

￥874,747 total

includes taxes & fees

Nov 3 - Nov 4

A building with a large entrance, potted plants, and a statue in the foreground.

16. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

Scott M.

￥285,194 total

includes taxes & fees

Nov 4 - Nov 5

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

Vaggio

￥182,263 total

includes taxes & fees

Nov 3 - Nov 4

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

Toscana

￥364,668 total

includes taxes & fees

Nov 3 - Nov 4

A villa with a swimming pool, surrounded by lush greenery and a scenic countryside view.

19. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

Montespertoli

"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!"

Elise D.

￥328,799 total

includes taxes & fees

Nov 3 - Nov 4

A person in a swimming pool with a view of a vineyard and hills.

20. "A Casa di Franca Villa con piscina"

Gambassi Terme

"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...

Anonymous traveler

￥268,560 total

includes taxes & fees

Nov 3 - Nov 4

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Top Castellina in Chianti Hotel Reviews

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."

Hotel Albani Firenze

8/10 Good

"The hotel was at a Good location. However, we stayed on the corner of 4th floor. We had to take 3 steps down upon entering the room. We only had a skylight with no actual window on the wall to look outside. The biggest problem was the room was really hot even with the ac on the coolest temperature setting. We had to open the skylight and we were still hot and couldn’t sleep at night."

aparto Florence Manifattura

10/10 Excellent

"We were pleasantly surprised by the size of our room, the size of the beds, and how comfortable they are. Super clean rooms. No breakfast, or near by places where to have a good cup of coffee, no refrigerator, or tea kettle in the room, no hair dryer either. Overall a great place to stay on a budget friendly hostel."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	191
Accommodation	1812 Villas
Lowest Price	￥21,802
Highest Price	￥2,489,733

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between ￥21,802 and ￥2,489,733 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 1812 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.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. Rooster House, Cooking Classes, and Opera

2. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

3. Villa Montecastello

4. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

5. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

6. Villa Capanna: A Window onto Tuscany

7. Villa Torre Among the Hills of Siena

8. Villa Mami: A Tuscan retreat full of elegance and charm

9. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

10. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

11. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

12. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

13. Exclusive Estate | Personal Concierge & Heated Pool

14. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

15. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

16. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

17. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

18. SwimmingPool ONLY FOR YOU in Villa with AirCon for 26/30 pax in 13 bedrooms

19. Luxury,Charming,in true Chianti, sleeps 22 or +/- pople., with AIR-CONDITION!!!!

20. "A Casa di Franca Villa con piscina"

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hu Firenze Camping In Town

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

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