Castellina in Chianti Villas Rentals

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

$135 nightly

Nov 14 - Nov 15

Total with taxes and fees

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.

$1,199 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

3. Villa Montecastello

Monteriggioni

Alvaro

$352 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$8,465 nightly

Nov 12 - Nov 13

Total with taxes and fees

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.

$1,731 nightly

Nov 15 - Nov 16

Total with taxes and fees

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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

Toscana

$2,909 nightly

Nov 16 - Nov 17

Total with taxes and fees

A large estate with a swimming pool, tennis court, and multiple guest rooms.

7. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

$13,178 nightly

Nov 29 - Nov 30

Total with taxes and fees

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,658 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

9. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,658 nightly

Nov 12 - Nov 13

Total with taxes and fees

A dining area with a wooden table, white chairs, and a chandelier.

10. Villa Liberty in The Centre - No Ztl

Siena Historical Center

$335 nightly

Nov 18 - Nov 19

Total with taxes and fees

A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Certaldo - Firenze

Kelly C.

$1,298 nightly

Nov 15 - Nov 16

Total with taxes and fees

A villa with a swimming pool, surrounded by lush greenery and vineyards.

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

Montespertoli

$6,031 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

13. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

impruneta

Oli P.

$1,430 nightly

Nov 12 - Nov 13

Total with taxes and fees

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.

$1,576 nightly

Nov 29 - Nov 30

Total with taxes and fees

A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

15. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

$15,814 nightly

Nov 14 - Nov 15

Total with taxes and fees

A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

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

Rignano sull'Arno

$5,552 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

$1,172 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Montespertoli

Scott M.

$1,809 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

19. "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

$1,702 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

20. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Careggi Rifredi

robert g.

$10,543 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

Hotel Albani Firenze

10/10 Excellent

"Excellent classic hotel. Gym could use a little more love. Breakfast was excellent but the same every day. Could use a little more variety."

Grand Hotel Cavour

10/10 Excellent

"Would give more than 5 stars if I could. This is my second time staying here and I've loved it both times. Came with family this time and everyone was pleased with the rooms which were clean, spacious, and well suited for family. The staff was always so accommodating, helpful with recommendations for food, and very professional. The location is perfect, and the rooftop bar is a nice bonus. We will def come back!"

Hotel Galileo

10/10 Excellent

"This was a great hotel! The rooms were small but adequate as we were not in them much. It is close to a great market and square with many food choices. The room and bathroom were clean and all amenities were as expected. We did not try to use the air conditioning so I’m not sure about its effectiveness, but we did open the window for some cooler air which also let in a lot of noise from the street. Would absolutely stay here again when in Florence."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	179
Accommodation	1813 Villas
Lowest Price	$138
Highest Price	$15,814

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between $138 and $15,814 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 1813 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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Villas in Castellina in Chianti

Bundle & Save

OneKeyCash

Upfront pricing

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 Mami: A Tuscan retreat full of elegance and charm

7. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

8. Villa Capanna: A Window onto Tuscany

9. Villa Torre Among the Hills of Siena

10. Villa Liberty in The Centre - No Ztl

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

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

13. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

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

15. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

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

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

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

19. "A Casa di Franca Villa con piscina"

20. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Albani Firenze

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia