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

1. Villa Montecastello

Monteriggioni

Alvaro

$163 nightly

Oct 24 - Oct 25

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

Amber M.

$1,667 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

3. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

$144 nightly

Oct 23 - Oct 24

Total with taxes and fees

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

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

Gaiole in Chianti

Bernard K.

$2,041 nightly

Nov 3 - Nov 4

Total with taxes and fees

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

$7,864 nightly

Oct 23 - Oct 24

Total with taxes and fees

A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$499 nightly

Oct 23 - Oct 24

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.

7. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,751 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

8. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,751 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

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

Certaldo - Firenze

Kelly C.

$654 nightly

Oct 23 - Oct 24

Total with taxes and fees

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

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

Toscana

$3,073 nightly

Oct 23 - Oct 24

Total with taxes and fees

A modern house with a swimming pool, outdoor seating, and a view of mountains.

11. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Vaggio

$830 nightly

Nov 2 - Nov 3

Total with taxes and fees

An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Florence

melissa r.

$370 nightly

Nov 1 - Nov 2

Total with taxes and fees

A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

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

Montespertoli

Krista G.

$2,173 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

14. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Oli P.

$1,239 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

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

Montespertoli

$6,054 nightly

Oct 26 - Oct 27

Total with taxes and fees

An outdoor patio with a round table and chairs, surrounded by a wooden fence and a large canopy.

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

Vaggio

$1,159 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

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

Montespertoli

Scott M.

$1,816 nightly

Nov 2 - Nov 3

Total with taxes and fees

18. Villa Sunset, in the heart of Chianti area

Greve in Chianti

elisa b.

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

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

$14,606 nightly

Oct 30 - Oct 31

Total with taxes and fees

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

$1,709 nightly

Nov 9 - Nov 10

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

Villa Neroli

10/10 Excellent

"My family and I stayed at Villa Neroli for three nights in October while celebrating our wedding in Tuscany and we really loved our stay! The hotel itself is beautiful with comfortable, clean rooms and lovely grounds. Breakfast was great, with plenty of options and the location worked really well for us with some nice restaurants nearby. What stood out most was the staff. Everyone was so friendly and helpful, especially the front desk team. We had quite a few requests during our stay, and they were always happy to help. We also had several family members and friends staying at the hotel for our wedding and the staff did a great job accommodating everyone and helping coordinate our wedding shuttle. One of our favorite moments was simply sitting outside by the pool one evening enjoying a glass of wine together. It was such a peaceful spot and a nice break from all the wedding excitement. Overall, we had a fantastic experience and really appreciated how welcoming everyone was. We'd happily stay at Villa Neroli again next time we're in Florence. Highly recommend!"

Hotel Paris

10/10 Excellent

"The hotel's location was great, a short walk from the train station and many tourist sites. The room was very large and clean. The bed was comfortable and the air-conditioning worked very well. The bathroom was also very large with a full counter. The shower was very nice, too. It was always great to come back to our room after walking all around Florence."

Hotel Horto Convento

8/10 Good

"Hotel Horto Convento provided a wonderful experience and allowed me to fully rest and recharge during my travels through Italy. The hotel itself is incredibly comfortable and remarkably quiet, offering a peaceful retreat. The location is excellent—it is an easy walk to downtown Florence, and there are plenty of outstanding restaurants nearby. To top it off, breakfast was included in the stay, and the fresh cappuccinos were absolutely fantastic. I highly recommend staying here!"

The Market Urban Hotel

10/10 Excellent

"The location of the hotel was very convenient to walk from the train station and to visit the city. The staff, in particular Giovanni, were very helpful. Giovanni really helped us navigate and discover interesting locations to visit and recommended the best shops. The room is small for two. But not unexpected in this type of European city. We had a wonderful stay."

Hotel Galileo

8/10 Good

"We had a good stay at Hotel Galileo and it worked really well for a short visit to Florence. The hotel feels smaller and more personal, which we actually liked. The location is convenient and close to a busier part of the city, so there was some street noise, but that was to be expected. The room had everything we needed, the hotel was comfortable, and overall it was a solid place to stay for a few nights. If you’re looking for something simple, well-located, and practical for exploring Florence, this is a good option."

Hu Firenze Camping In Town

10/10 Excellent

"On a bien aimé notre séjour. C’était très propre partout. Notre cabine était parfaite. Votre équipe s’est bien occupée de nous. Et nous avons eu un très bon service. Nous le recommandons. Et le restaurant et le service était très bon aussi. Nous avons trouvé très pratique de pouvoir acheter nos excursions au camping et d’avoir le transport pour les excursions directement du camping c’était bien pratique et zéro stress à essayer de trouver le groupe au centre ville."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	331
Accommodation	1829 Villas
Lowest Price	$147
Highest Price	$14,606

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between $147 and $14,606 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 1829 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

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OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. Villa Montecastello

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

3. Rooster House, cooking classes and opera

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

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

6. Villa Il Signorino

7. Villa Capanna: A Window onto Tuscany

8. Villa Torre Among the Hills of Siena

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

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

11. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

12. Luxury Villa in the Florentine hills

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

14. Exclusive Estate | Personal Concierge & Heated Pool

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

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

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

18. Villa Sunset, in the heart of Chianti area

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

20. "A Casa di Franca Villa con piscina"

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Villa Neroli

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia